


Paramount Remembrances

by FatesTemptress



Category: Supernatural
Genre: Dry Humping, F/M, First Time, First Time Blow Jobs, Light Angst, Light Dom/sub, Oral Sex, Smut, Teaching
Language: English
Status: In-Progress
Published: 2018-04-27
Updated: 2018-06-27
Packaged: 2019-04-28 17:39:58
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 9
Words: 36,154
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14454408
Author URL: https://archiveofourown.org/users/FatesTemptress/pseuds/FatesTemptress
Summary: Dean Winchester has reached a point in his life where he doesn’t have many firsts left to fulfill.  Except maybe falling in love.  This is the story of how he got there.





	1. Chapter 1

**Author's Note:**

> A/N: This one kind of got away from me and I’m currently at over 8,000 (:x) words and counting so I decided to break it up into chapters. Currently , we are looking at about maybe 4-5 Short Chapters of my yammering. I have most of it written and ready to post but I’m still obsessively going over it. Please note, I’m not sticking to canon timelines as rigidly as some wonderful writers do. Please take any errors in timeline continuity with a grain of salt. Many thanks! 
> 
> As I said before, I’m new to AO3 so if any of this posts incorrectly, I apologize. 
> 
> This will be Dean x Reader Eventually. We'll get there. Promise.
> 
> Please note, this is unbeta’d. Any and all grammatical errors are mine. (And I’m sure there are PLENTY. :))

Dean was seventeen when he got his first blow job. 

It was slightly awkward and the girl, Mandy, was only a little older than him and not exactly what you’d call experienced. 

If he was honest, the encounter was all saliva, teeth and swearing. 

But if you asked Dean at the time, it was fucking epic. 

The experience of sitting in the back of his father’s car, making out with the girl with the highest kick in the cheerleading squad as she let him run his hands anywhere he could reach, was _made_ for replay in his spank bank. 

God, she had been beautiful.

Dean had noticed her the first day he attended the high school in the Podunk Town his father forced him to grace with his presence. Her big blue eyes and her long dark hair made things in his lower belly tighten as she threw her head back in a laugh that showed all of her perfect white teeth. 

She was sitting towards the front of the classroom of his English class that he hadn’t planned on attending after today but would now make it a priority to be in his seat every god forsaken day.

It had taken Dean a couple of days to get her attention. But he had made sure to walk by her locker as often as he could with his long legs swaggering by, throwing her a wink when her blue eyes met his. 

It became obvious that his bad boy demeanor both scared and intrigued her. Especially in class when she would look up and catch him staring; her gaze meeting his before quickly darting away as she bit her full bottom lip. 

But Dean was nothing if not persistent. 

Soon, after a football game that he had attended just to see her kick those longs legs under that sinfully short cheerleading skirt, Dean waited for her sitting on the hood of his father’s car with his elbows resting on his knees and his hands clasped in front of him. She came out of the gates of the football field with her friends trailing behind her, giggling as they saw him sit up at the sight of her. 

“Go on Mandy.”

“It’s obvious he’s here for you.”

Mandy swallowed deep in her throat before making her way over to him, her pom poms still clutched in her hand, her eyes glittering with intrigue and nerves, “So…..you’re Dean right?”

He stood with his hands in his jean pockets, rocking back on his heels, a half smile gracing his face, “If I say yes, will you let me give you a ride home?”

After that night, they became inseparable; roaming the halls of the high school, holding hands, smiling at each other like there was no one else around them. 

And pretty quickly, Dean became entranced as Mandy’s shy smiles hid a girl who was all too happy to make out for hours on end, straddling him as she rubbed her jean covered core over his raging hard-on with abandon, rolling her tongue against his as pants huffed through her lips.

Dean was certain his dick was gonna fall off from rug burn pretty soon but he was all too happy to thrust up against her if it meant she made that low whine in her throat when he hit a certain spot. It was even better after football games when she was wearing nothing but her panties and those little white shorts that said ‘Go Team!’ in black letters across the back. She would leave wet spots all over his jeans as her eyes would roll into the back of her head and she’d throw her neck back so that he could suck along her pulse point. He’d grab at her ass and rhythmically push her against him until she shuddered with a low moan.

Dry humping was gonna kill him but fuck if those sounds she made didn’t help him once Dean got home and took his cock into his own hands. He’d rub himself with abandon until his own head was thrown back against his pillow as he pressed his lips together to keep his moans from leaking out into the night air as hot spurts of come covered his fingertips. 

Dean wasn’t exactly shy but he had been hesitant to push Mandy farther than she was ready for and he let her lead the way when it came to progressing to the next steps.

So, it was a torturous month later when Mandy straddled him and for the first time pulled down her tank top and led a dazed Dean over to one light pink nipple. The bud hardened in the cool confines of the Chevy and Dean looked up into her eyes once to make sure she really wanted this before running the tip of his tongue over the tip. He answered her loud groan with one of his own as he closed his mouth over it and sucked hard. After that, it was if she had lost her fucking mind and her shirt was ripped over her head as she wordlessly begged him to run his tongue over each breast by shoving them into his face as she grinded down on him. 

Dean lay his head in between her breasts and breathed heavily, trying his damndest not to flip her onto her back and beg her to let him slip inside of her. He had a feeling she wouldn’t say no, but he didn’t want their first time (his first time) to be in the back of his father’s car, “Mandy, you’re gonna kill me.”

Mandy placed both palms against his cheeks and raised his head to meet her eyes, “I’m sorry, Dean. I know _this_ has gotta be bothering you.” She reached down and grabbed him with her hand for the first time through his jeans and he was embarrassed by how loud he moaned.

“Fuck, Mandy.”

“Do you….do you mind if I try something?”

Dean blinked lust heavy eyes up at her and nodded without thinking as she reached for his belt buckle and dragged down his zipper carefully over his raging hard-on. His breathing picked up even more as she reached into his boxer briefs and pulled out his dripping cock, her eyes wide at the sight of him, before dragging her hand down to the base and bringing it back up. His hips involuntarily moved up into her strokes as for the first time a hand that wasn’t his own jerked him off. 

For some reason, letting go the way he wanted to made feelings of embarrassment course over his limbs so instead, his fingers dug into her hips as he desperately tried not to let out the low moans that wanted to work their way out of his throat. 

The silence should have been stifling, but the roar in his ears was enough to drown out all thought. 

However, it seemed as though his lack of voiced encouragement was making Mandy self-conscious, “Is this….is this okay?”

The drips of precome aiding Mandy’s progress should have been telling enough, and when she twisted her hand at the top of his cock just so, he saw stars and this time couldn’t stop the drawn out moan that escaped his lips, “Oh my _GOD_ , yes. Please…please don’t stop.”

Mandy let out a low whine as she picked up the pace of her fist paying particular attention to the tip. Dean leaned back into the backseat and proceeded to gasp into the humid air, “Fuck Mandy, I’m gonna….”

Suddenly his balls tightened up and it was as if an explosion rang through his ears as he came in long hot spurts all over Mandy’s pale fingers, unable to stop the loud, “Son of a bitch!” from leaving his mouth.

His gasps filled the car as he tried to come down from the euphoria of his first hand job. Somehow, someway, he was able to gather his scattered brain and reach down into the side of the door and hand some napkins to Mandy. 

His cheeks felt like they were on fire as they burned with embarrassment over his reaction, hoping against hope the beautiful girl sitting in his lap wouldn’t laugh at him.

“That was so fucking hot, Dean.”

Dean’s head sprang up at her words and a lazy grin smoothed its way across his mouth, “Yeah?”

“ _Hell_ yeah.”

The next time they were in the car, Mandy eagerly reached into his jeans as he smoothed a hand over her breast and pinched a nipple between his fingers. He hummed into her mouth as she quickly jerked him off before he winced slightly and stayed her hand, “Wait. It’s uh, a little, um, dry.”

Her eyebrows scrunched together before a wicked gleam passed over them, “I think I know what I can do to fix that.”

And before Dean could say anything else, Mandy was suddenly on her knees in the tight space between the front and back seats pulling his jeans down his thighs before her tongue darted out and licked a long line from the bottom of his shaft to the tip. 

“Holy shit!”

Not needing any further encouragement, Mandy swirled her tongue over the slit at the top of his cock and made a surprised sound when a salty bit of pre-come spurted out the top. 

Dean shuddered as he swallowed deep.

_He was not gonna come yet. He was not gonna come yet._

A hum sounded from Mandy, “Been thinking about this so much, Dean.”

“Wha-you have?”

She nodded, his cock leaning against her lips, her breath like tiny fingers caressing the tip. Her eyes were wide in the dark as she adjusted her grip, “Wanna make you feel as good as you make me feel.”

Before he could respond, her mouth opened and her lips slid over the top of his cock and she sucked the head into the roof of her mouth. Her teeth inadvertently scratched against the tip but before he could warn her she swallowed down as much of his shaft as she could manage and he moaned as he ran his fingers through the silky strands of her hair. He struggled not to thrust into her mouth as she started bobbing her head up and down his shaft, dribbles of saliva making their way onto his ball sack.

_Shitshitshitshitshit._

Mandy let go of his cock with a pop, saliva glistening in the corner of her mouth, and looked up at him with earnest blue eyes, “You can let go, Dean. Just let me know, okay?”

With a jerky nod, he sifted his fingers deep into her hair as she placed small licks over his cock, her little pink tongue darting all over the place as if she didn’t want to miss one section of skin. Looking up into his eyes, she opened her mouth wide and swallowed him down with a confidence that should have surprised him.

He threw his head back against the seat and swallowed but couldn’t help the words of encouragement that slipped out, “Fuck, Mandy. So good.”

At his words, she moaned and quickened her pace and that was all it took, “Oh my God. I’m gonna-I’m gonna come. Mandy, baby, please-.”

Sound was sucked out of his ears and all that was left was a ringing sound as his hips jerked up and into her throat, the guttural moan that left his lips perhaps a touch too loud as ropes of come spurted into the heat of her mouth and then into the air as Mandy jerked her head back from the onslaught.

“Holy…I mean…that was…shit…”

Mandy giggled as she wiped at the come on the corners of her mouth, “I can’t wait to do that again.”

Turns out, that time would never come as the next morning his father came home and packed Dean and Sammy up and out of the town in two hours flat. 

Dean desperately tried to convince his father to let him take the car to ‘grab something from his locker at school.’ 

John gave him an eyebrow at his blatant lie and leaned against the car with a sigh, “You’ll learn it’s better to not make connections, son. All you’re gonna do is love ‘em and leave ‘em. What we do is more important than a piece of tail.” He pushed himself off and motioned to the Chevy, “Now get your ass in the car and let’s go.”

Dean’s heart sank, but the soldier in him didn’t know how to put his foot down against his father, “Yes, Sir.”

With one last look towards the center of town, Dean whistled to his little brother, “Come on, Sammy. Get in the car.”

**~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

Dean was eighteen when he lost his virginity.


	2. Chapter 2

**Summary for the Chapter:**

> Dean Winchester has reached a point in his life where he doesn’t have many firsts left to fulfill. Except maybe falling in love. This is the story of how he got there.

**Notes for the Chapter:**

> Pairings: Young Dean x OFC, Dean x OFC, Dean x Reader (Eventually) (Promise!)
> 
> A/N: Here we go! Part Two! 
> 
> Please note, I’m not sticking to canon timelines as rigidly as some wonderful writers do. Please take any errors in timeline continuity with a grain of salt. Many thanks! 
> 
> As I said before, I’m new to Ao3 so if any of this posts incorrectly, I apologize.
> 
> Please note, this is unbeta’d. Any and all grammatical errors are mine. (And I’m sure there are PLENTY. :))

Dean was eighteen when he lost his virginity. 

The back of the Chevy that his father had officially gifted to him on his eighteenth birthday has seen a hell of a lot of action. But the night Dean first slid into his first wet pussy would easily go down in history as one of the best on the sizzle reel. 

Her name had been Gillian. 

Such a sweet name for such a dirty girl.

His dad had left him and his brother behind and took up with another hunter friend on a tough case wanting to keep them out of the more dangerous hunts until he felt they were ready. 

One evening, with Sammy at the town library studying God knows what, Dean had made his way down the road to the diner closest to the motel they were staying at. He sat down at a corner booth, looking out the window, bored out of his mind, when a sweet voice interrupted his musings.

“Hi, I’m Gillian. What can I get ya?”

Dean turned his head and looked up into the sweetest hazel eyes this side of Texas. Her long red hair was gathered into a side ponytail and curled softly down the front of her waitress uniform. Her small waist led to a curvy set of hips that immediately made things inside of him tighten.

A slow smile spread across his face and he watched as she bit the bottom of her lip as he tilted his head and looked up at her, “The special, please.” 

She blinked down at him, “Uh, yeah sure. Coming right up.”

One special and three coffees later, Gillian was off work and taking Dean on a tour through town, telling him about her plan to get the hell outta dodge the second she graduated from college in a year. 

Two nights later, in his car, on some cliff overlooking some lights that Dean never got to appreciate, Gillian sat beside Dean in the backseat as she led his hand under her skirt and over her soaked panties as his tongue licked its way into her mouth. 

His fingers hesitated for the slightest of seconds. He had never touched a girl down there before. Sure, he had rubbed his jean covered dick against an equally covered pussy, but he and Mandy never got as far as him actually putting his fingers on her.

But when Dean rubbed his way over Gillian’s soaked white panties and she reached down and pulled them to the side for him, he was hooked.

Gently, he rubbed his fingers over her folds and swallowed her erratic breaths as he slid his middle finger down to her waiting hole.

Should he? Shouldn’t he?

Gillian answered the question for him as she canted her hips into his touch and whined when the tip of his finger entered her. When he still hesitated, she reached down and pressed his middle finger in deeper and moaned into his mouth, her tongue darting out and wrapping against his as she kissed him deeply.

“Fuck.” He whispered into her mouth as he slowly started moving his hand, savoring the feel of her slick running down his finger onto his hand.

Gillian broke the kiss and moved her hips into his motions, her harsh breaths grazing along his lips as she met his eyes with intensity. With a low groan, Dean licked his way down to the swell of her breasts and she immediately started unbuttoning her shirt and threw it somewhere behind her. Her white lacy bra glowed in the moonlight and he pulled down the cup with his free hand to suck her nipple deep into his mouth. 

Before he could contemplate his next move, Gillian was pulling back from him as she shimmied out of her panties. Quickly, she unbuckled his belt and pulled down his jeans, “Need you now, Dean.” 

Dean lifted his hips, “Ummm, o-okay.” He answered as he helped her bring his jeans down to his ankles.

Gillian lifted an eyebrow at him as she took in his dick, “Well _that_ is pleasantly surprising.”

Dean blinked at her and let out a small huff, “Uh, thanks?

She reached behind her and undid her bra throwing it in the same direction as her shirt, “You got a condom, right?”

“Uhhh, yeah, in my, uh, wallet.” 

The same condom his dad had given to him when he had turned eighteen along with a long embarrassing speech about safe sex and the rules of the road. 

As he fumbled through his jacket pockets, looking for his wallet, sweet Gillian leaned over and engulfed his cock in one smooth stroke, careful to put her lips over her teeth. Immediately, his fingers gripped the leather of his jacket in a death grip as he tried to keep his composure. 

Mandy had been sweetly naive. 

Gillian on the other hand knew what the fuck she was doing. 

And she was doing it well.

Too well. 

When she pulled up his cock and started tonguing his sack he knew he had to stop her. He was milliseconds away from spurting into her face and God knew he wanted to come inside of her instead.

“Gill-Gillian. Sweetheart, you gotta stop.”

Gillian hummed and rolled her eyes up at him as she gave his balls one last swipe, “Eager to fuck me, are we?”

Dean nodded jerkily and finally pulled out the condom from his wallet. He had a moment of pure panic as he pictured himself fumbling with the slippery thing, struggling to put it on but it seemed it was for naught as Gillian plucked it out of his hand and quickly ripped open the package and rolled the condom on with a practiced hand.

The moment of truth was upon him and he half expected someone to start knocking at the window, stopping him from losing the virginity that he felt should have been left behind a hundred towns ago. (Life on the road, taking care of a sibling, didn’t really amount to a lot of personal time.) 

Lucky for Dean, the only knocking that sounded was the rapid beat of his heart as Gillian tugged on his t-shirt and ripped it over his head. Oddly enough, she kept on her skirt, the only piece of her clothing left, before simply raising it up as she threw her leg over his lap and straddled him. Holding her skirt with one hand and grabbing his cock with the other she lined him up with her core and slowly slid him in inch by inch as she mewled at the stretch.

Dean’s eyes crossed as the searing heat enveloped his cock and it took everything in him not to come right then and there. 

“Oh, fuck that’s good.” Gillian moaned as she bottomed out.

It was the most amazing feeling in the world and nothing in his life had ever topped this moment.

Or at least nothing had until Gillian started to move her hips and slid his cock in and out of her wet heat. 

The sound that came out of Dean’s throat should have been embarrassing but it was quickly overshadowed by the high-pitched whines coming out of Gillian’s mouth. 

Dean wished he could say he lasted a long time. That he was a stallion. But having your first wet pussy roughly pounding out on your virgin dick, didn’t exactly give a guy stamina.

Lucky for him, someone in heaven must have liked him, because Gillian was one hell of an orgasmic chick and came about two point five seconds before he raised his hips is abandon meeting her rough thrusts as he squeezed his eyes shut and came with a loud groan that paled in comparison to her screams.

_Holy shit._

Dean came out of his stupor to Gillian placing warm wet kisses up and down the column of his throat, before she nipped at his ear and whispered, “Let’s do it again.”

When he was able to formulate sentences, he had to tell her that he only had the one condom. Luckily, Gillian was a paragon for safe sex and had condoms of her own in her purse.  
They had stayed in that town for two weeks. 

Dean had fucked Gillian left, right and sideways, every chance he got.

One time he had even had her in the diner’s kitchen after closing. Bending her over the stainless-steel countertop as she begged him to go harder and harder until he had exploded with a loud grunt that left him on shaky legs.

Another time, Gillian showed Dean just how dirty she really was as she begged him to come in her mouth and on her face so she could swallow and swipe up his extra essence with her fingertips before bringing it into the hot cavern of her mouth with a humm. 

She had certainly taken his virginity with a bang. 

And then he had to leave her.

It was somehow easier this time.

Gillian knew he was a drifter and expected nothing more from him than what he gave and when it was time to say goodbye, she looked him in the eye and told him, “See ya around, Winchester.”

~~*~*~*~*~*~*~*~*~*~*~*~*~*~*

Dean was nineteen when an older woman taught him how to eat a girl out.


	3. Chapter 3

**Summary for the Chapter:**

> Summary: Dean Winchester has reached a point in his life where he doesn’t have many firsts left to fulfill. Except maybe falling in love. This is the story of how he got there.

**Notes for the Chapter:**

> Pairings: Young Dean x OFC, Dean x OFC, Dean x Reader (Eventually) (Promise!)
> 
> A/N: Here we go! Part Three!
> 
> Please note, I’m not sticking to canon timelines as rigidly as some wonderful writers do. Please take any errors in timeline continuity with a grain of salt. Many thanks!
> 
> As I said before, I’m new to Ao3 so if any of this posts incorrectly, I apologize.
> 
> Please note, this is unbeta’d. Any and all grammatical errors are mine. (And I’m sure there are PLENTY. :))

Dean was nineteen when an older woman taught him how to eat a girl out. 

He had been helping his dad gather up information on a case, posing as a college kid who worked for the school paper. When he went to interview one of the women who witnessed objects flying around a room on their own in her friend’s house, he figured he’d see a housewife with an apron on and a spatula in hand. 

Instead, the woman who had opened the door had been breathtaking. 

Her bright green eyes had practically fucking sparkled and her silky long brown hair had surrounded her face in waves. Her body was encased in a stretchy black pencil skirt with a white button up tucked in. The highest pair of black heels Dean had ever seen on a woman finished off the outfit and it wasn’t hard to picture them up in the air and over his shoulders. 

A dazzling smile shot out at him as she placed an earring in her ear, seemingly in the midst of getting ready to go out, “Hi, can I help you?”

“Ummmm, yeah, Mrs. Lyla Fitzgerald?”

She smiled again, “Ms. Lyla Fitzgerald, actually. But yes, what can I do for you?”

Dean scratched behind his ear as he nervously adjusted his jacket, “I, uh, my name is Dean and I work for the college paper and I was wondering if you’d have the time to answer a few questions about the strange occurrences at your friend Jackie Silverstein’s house.”

Lyla gave him a good look from the bottom of his scuffed boots to the tip of his slightly indented nose before opening the door, gesturing for him to come in.

A wave of expensive perfume hit his nose as he passed her, and Dean took a deep breath of it in, “Thanks for sparing some time for me Ms. Fitzgerald. I appreciate it.”

“Please. Call me Lyla.” She led him to her kitchen and gestured to the breakfast bar where there were four bar stools, “You’re making a twenty-eight-year-old feel like she’s in her fifties.”

Dean let a lazy grin slide over his face, “Apologies, Ms., uh, Lyla.”

She leaned over the counter on the other side of him, effectively affording him a view down her white button-down shirt and he had to force his gaze back up to her amused, knowing ones.

“No apologies necessary, Dean. Now, what can I do for you?”

Turned out there was a lot she could do for him. 

Lyla had invited him back to the house that night stating she had something for him that may help his article. 

She had answered the door with nothing on but a short silky black robe, those sexy as fuck heels and a glass of white wine in her hand. 

Needless to say, when she had smiled and reached up to bring his lips down to hers, the sweet taste of wine on her tongue permeating his mouth, he hadn’t stopped her.

And when she leaned over the kitchen counter and lifted that silk black robe to reveal her clean-shaven pussy, Dean had eagerly run his fingers over her folds before taking her against the counter.

Later, in her bedroom, after having had those black heels by his ears as he had mouthed at her smooth calf and thrust in wild abandon into her wet core, Lyla turned to Dean and licked at a droplet of sweat on his neck, “I wanna come again.”

Dean let out a small laugh, “You’re gonna have to give me a few minutes, Sweetheart.”

She licked down his chest and swirled a tongue over his flat nipple, “Just eat me out, honey. And then when you’re ready we’ll fuck again.”

A blush ran up his face and he swallowed hard, “I, uh, haven’t ever, I mean…”

Lyla sat up and stared at him, “You’ve never gone down on a woman before?”

He cleared his throat, “Uh, no.”

“Well, do you want to learn?”

His eyebrows scrunched together as his embarrassment was quickly overruled by intrigue, “You’d do that?”

“Oh honey, I will be happy to give you the gift that keeps on giving.”

The next thing he knew he was leaning up against her headboard, with her back leaning against his chest and her firm body tucked in between his legs, a wet washcloth in her hands as she guided his hand over core, “We’re gonna make sure you’re first experience is memorable. Trust me if you’re not ready for it, the taste of condom isn’t cute.”

He nodded watching over her shoulder as the white washcloth rubbed against her hairless pussy, wiping away the essence of their earlier coupling, and he couldn’t help but bring his free hand up to her bare breast and pinch a nipple in between his thumb and forefinger.

“Mmmm, that feels good.” Lyla purred and threw the washcloth somewhere on her bedroom floor, “Now, first things first. Let me introduce you to the most important part of a women’s anatomy. The clitoris.”

She brought a hand down and separated her folds with two fingers, “You see that little bud right there? If you rub or suck it just right, you can make a woman’s eyes cross. Now give me your hand.” Lyla guided his long fingers over to her mouth, “Nobody likes a dry pussy.” She tilted her head back to look at him as she sucked his three middle fingers into her mouth and licked at the pads with a practiced tongue and Dean could feel his half hard cock swelling to full size.

“Fuck, Lyla. That’s hot.”

She hummed around his fingers before letting them go with a pop and bringing them to the now hard button at the top of her heat. She helped him press down and roll his fingers over it as her hips canted up slightly into the movements, “Start out nice and slow. This is a sensitive area and some women can’t even have direct pressure on it. Always, always pay attention to your partner’s reactions.” 

Dean leaned his chin on her shoulder watching his fingers intently, his breaths leaving in jagged puffs of air, “You seem to be just fine with it.”

“Mmmm, that’s cause I’m a woman who loves it hard and rough. Not all of those college girls will be able to appreciate a good hard fuck just yet. Now, let’s bring your fingers down to the hole and dip them in. Oh, yeah, just like that. Let’s get all that wetness and bring it back to the top. Press a little harder this time.”

Soon, Dean could feel how big her clit had swelled as he finger fucked her with one hand and rubbed at the top of her heat with the other. His hips were moving involuntarily as he rubbed his hard cock against her back. Meanwhile, Lyla had thrown her head against his shoulder and was thrusting her hips into his touch, her hands caressing her breasts and pinching at her hard nipples.

“Such a good student. That feels so fucking good.” She moaned one last time before reaching down and staying his hands. She picked up one of his slick laced hands and brought it to his mouth, “Taste it. If you can’t handle this part, then you won’t be able to eat a girl out properly. You have to love it. ‘Cause when you eat a pussy you gotta have your tongue and mouth all up in there.”

Dean obediently opened his mouth and tentatively licked at his fingers. The salty, sweet taste hit his taste buds and he hummed and opened his mouth wide and, much to Lyla’s delight, sucked the rest of his fingers in, licking away every piece of her essence he could find.

Oh yeah. He could definitely fucking do this.

“Can I-can I eat you out now?”

Lyla’s eyes closed as she shifted her legs against the ache in her core, “Get your ass down there already.”

Dean eagerly slid his way out from behind her and lay on his stomach in front of her open legs, “Okay. What do you want me to do?”

A small laugh left Lyla’s lips as she looked down into Dean’s grin. She caressed his cheek in her hand before pulling him towards her, “Give me one long lick first. Start from the bottom to the top. Then suck right here. Hard.”

Dean stared into Lyla’s core with a little bit of apprehension. He wanted to do this. But he wanted to do it right. 

Lyla seemed to sense his hesitation and reached down and opened herself up to him, “Right here, Honey. Put your tongue here first.”

Dean looked up into her eyes and gently placed her legs over his shoulders. At her encouraging wink, he leaned forward and opened his mouth and stroked his tongue just as she asked for before sucking her clit into his mouth. 

It was so erotic yet so intimate. Putting his mouth on her core, tasting her sweet and salty essence, feeling her legs tense around him in pleasure as she leaked more of her excitement onto his tongue; all of it made his cock swell even further and he groaned against her as he rolled his tongue around her clit and sucked again.

Lyla let out a deep breath, “Mmmm, just like that, Honey.” 

It wasn’t too long later that Dean had two fingers deep inside Lyla’s soaking wet core, rubbing against the rough spot she had led him to, rapidly moving them in and out as he eagerly sucked and licked at her clit, moaning as she grabbed at the short strands of his hair, “Oh my God. Yes! Take your other hand and rub right there with your thumb. Harder. FUCK YES!”

Lyla’s hips thrust up into Dean’s face as she came, her body shuddering in completion. She rolled her hips against his tongue once more before stopping him, “Okay, okay.” She gasped out, “Very sensitive.”

Dean licked his lips and grinned up at her, “Sooooo….was that good?”

She smiled back, “Fucking awesome. You’re a natural. I’ll give you an A plus plus.”

He sat up and fist pumped into the air making Lyla laugh at his antics, until her eyes strayed down to the leaking hard-on he was sporting, “Looks like someone is ready to make another appearance. Come here.”

Dean spent the rest of the night being fucked and sucked into a different dimension. He left Lyla’s house two days later with a new appreciation for a woman’s body and with skills that would stay with him for life.

His father had solved the case without him, sans any notes Dean may have provided.

It had been worth having his father berate him for hours about disappearing and being responsible about checking in. He had listened and nodded and Yes Sir’d at all the right times. 

But inside he was smiling so hard he was surprised he wasn’t fucking glowing. 

*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~~*

Dean was twenty-three when he learned the old adage, “Be careful of the quiet ones.” was true.


	4. Chapter 4

**Summary for the Chapter:**

> Dean was twenty-three when he learned the old adage, “Be careful of the quiet ones.” was true.

**Notes for the Chapter:**

> Please note, this is unbeta’d. Any and all grammatical errors are mine. (And I’m sure there are PLENTY. :))  
> Please note, I’m not sticking to canon timelines as rigidly as some wonderful writers do. Please take any errors in timeline continuity with a grain of salt. Many thanks!

Dean was twenty-three when he learned the old adage, “Be careful of the quiet ones.” was true.

He had been researching a case in a library located in a big city and his eyes were crossing. Dean couldn’t say he hated research but he sure as hell didn’t love it all the time. The plus this time was he had a huge library to work with. It had three floors of books and plenty of space to spread out his obscure books on occult and lore. 

Dean was on his fifth book with a small blurb on Ghoul lore and he still wasn’t getting the answers he was looking for. With a sigh, he closed the dusty tome in front of him and stood up to place it back on the shelf. He ran his fingers over the bindings of the other books on the shelf looking for something that would catch his eye when he stepped right onto the toes of a black ballet flat.

“Dammit. I’m so sorry.” He said as he grabbed onto the owner of the ballet flats shoulders.

A petite blonde girl with a pony tail looked up with smooth pale skin and wide eyes obscured by a pair of black rimmed glasses and nodded her head quickly, “s’okay.” She practically whispered.

Dean looked down and noticed the leather bound book she had gripped tightly in front of her pink button down sweater, “Hey, is that a mythology book?” 

The blonde nodded her head, looking down at her shoes. 

Dean’s eyes scrunched together as he took in her stance. She was cute in a bookworm kind of way. Probably around twenty-one or twenty-two. Her close fitting black slacks, were held up with a black belt and her white blouse was tucked into them with that pink sweater over it. Her shoes looked shiny despite where he had stepped on them. Not a scuff on them. She was neatly put together. Not a speck out of place.

And she looked so painfully shy that something in Dean’s heart tugged.

When she continued to refuse to meet his eyes, he cleared his throat and bent his head, forcing her gaze to his, “Hey. I’m Dean. I’m doing a research paper on some pretty obscure lore. Are you familiar with any of the stuff in the book you’re holding?”

Chocolate brown eyes blinked back at him and she worried her pink bottom lip before nodding, “Yeah.” She said almost too low for him to hear, “I-I’m taking a Mythology class th-this semester.”

“Awesome! Maybe you can, you know, help me out?” When she hesitated, he gave her his version of Sam’s puppy eyes, mentally crossing his fingers that they would work, “Please?”

Biting her lip again, he could see her holding back a smile.

“Pretty please, with a, I-promise-I’m-not-a-stalker on top?”

At his words, the smile finally slid across her mouth and he was graced with the cutest dimples he had ever seen on a girl, before she answered, “O-okay. M-my, uh, my name is Addison.”

For the next two hours, Addison stuttered her way through Dean’s questions on the lore he was looking for. Her quiet answers forced him to sit closer to her than propriety recommended and her light perfume tickled his nose as her soft giggles made him smile. 

When he had gathered as much info as he could possibly think of, he gathered up the books into a pile, “I appreciate this so much, Addison. Can I buy you a cup of coffee as a thank you?”

Addison pushed up her glasses and smiled shyly at him, “Ho-how about a drink instead?”

With a raised eyebrow, Dean accepted.

Turns out dark rum made Addison’s stutter go away.

It also made her horny as hell.

They had been sitting in the corner of a dark bar full of loud music and local college students and innocent little Addison was on her third rum and coke and it didn’t look like she was anywhere near intoxicated yet. 

Apparently, Addison was no light weight.

By the first drink the only difference between library Addison and bar Addison was that she spoke a little louder, laughed a little harder. By her second drink she was leaning into Dean’s space and instead of that lip bite looking innocent she was making it look like an ad for a dirty movie. By the third drink, her pink sweater was off, they were facing each other on their bar stools and her hand was squeezing his knee when she laughed at some story he told.

Dean was trying his best to tell the pest in his pants that this wasn’t going to happen but apparently Addison didn’t get the same memo and leaned even closer to him before sliding her hand all the way up his thigh as his breath hitched. It was promptly released when she bypassed his now semi interested midsection and instead grabbed onto one of the belt loops on his hip. 

“What’s the matter, Dean? You look a little nervous.”

Dean huffed out a breath, “Who me? Nah.”

She shifted off the bar stool until she was standing in between his legs and looked up at him, so close to his mouth, he could smell the sweetness of the rum on her breath, see the image of himself reflected through her glasses, “You sure? I’d hate to make you feel…uncomfortable.” She said as she grabbed a belt loop on the other side of his waist and pulled him up against her stomach.

“Uh…heh….You know…not really feeling uncomfortable as much as confused.”

She raised an eyebrow before hovering her lips over his, “Yeah? Maybe this will help you understand.” 

Her mouth promptly closed over his and for a second Dean didn’t know how to respond as his hands waved in the air around her body, his mind sure she would push him away and run screaming, but when her tongue slipped over his lips asking for entrance, his body suddenly remembered how to react. One arm slipped over her waist and brought her petite frame even closer to him as he opened his mouth and allowed her tongue to tangle with his.

Addison didn’t run away. Instead, she broke the kiss and slid her lips to his ear, “I bet you have a big cock.”

Dean’s eyes widened and he choked on his own saliva and coughed, “Pardon?”

He heard Addison giggle in his ear as she bit down on the lobe as one of her small hands was rubbing up and down the now prominent bulge in his pants, “Show me yours and I’ll show you mine.” 

Next thing he knew he was throwing money down on the bar before Addison dragged him down the street to her small apartment. 

The door had barely closed behind them, when she stepped into her methodically arranged, so clean everything was shining, living room and practically ripped open the buttons of her white button down, revealing the sexiest baby pink bra he had ever seen. The cups of the bra were cut in such a way that her nipples were resting on top them instead of inside.

“Oh…wow.”

She hummed and giggled again before kicking off her flats and reaching for the belt and button of her pants, shoving them down her legs and kicking them off to the side. The matching satin, barely there, pink underwear was shiny and already he could make out a wet spot.

“If you like the bra, you’re gonna _love_ these crotch less panties.” She purred.

Dean gulped as his eyes widened. He guessed it was a moot point to even ask if she was sure she wanted to do this. 

Soon, he found himself in her bedroom, down to his boxer briefs tonguing at her taunt nipples as she squirmed underneath him. “Oh my God. Lick them, baby. Use your teeth. Fuck! So good!”

As his quickly failing brain was trying to match up the meek girl from earlier today with the undulating, dirty mouthed woman underneath him, Addison nudged him up and opened her legs giving him an up close and personal view of the aforementioned crotch less panties. She reached down and rubbed at the wet spot on the top of her heat before dipping her finger inside of herself with a mewl. She removed her finger and held it up to his lips, moaning as he immediately sucked it into his mouth, “You can take off the panties once you make me come with that mouth of yours. Make it good enough and I’ll show you my non-existent gag reflex.”

Never one to back down from a challenge, Dean reached for her legs and dragged her down to the edge of the bed before throwing them over his shoulders, “Better get that throat ready for me, Sweetheart.”

Before she could retort he was burying his nose into her wet folds, licking and sucking his way up to the covered portion of where her clit was and scraping his teeth over the silky material making her shudder. He stabbed at her hole with his tongue before placing his whole mouth over her sex and sucking hard.

Addison arched her back, “Oh shit! Fuck!”

Dean groaned against her pussy as her body released more slick into his mouth. He brought two fingers up to her heat and reached in looking for the sweet spot he knew would make her eyes cross. When she squealed and pushed down into his fingers thrusts, he knew he had it.

Her breaths were coming in loud gasps that matched the speed of his fingers and her mouth spewed more dirty words by the second, “Oh, yes. Eat this pussy, baby. Oh Fuck! I’m gonna come. Right there! YES!”

Her legs tightened around his head as she came with a scream that he was sure was going to bring the cops to the door as he lazily licked over the now soaked material.

Breathing heavily, she finally released him from her vice grip and sat up, “That was a new record. No one has ever made me come that fast.”

Dean gave her a cocky grin but didn’t say a word as she pulled off her panties and bra and placed them neatly on the bed beside her. She kept her eyes on him as she made her way to the edge of the bed on her knees before turning around onto her back and lying with her head hanging off of it.

“Uhhh, Addison? What are you-.”

“Take off your underwear and come here.”

Following her direction, Dean eventually ending up standing over face, his eyebrows scrunched in confusion, as she opened her mouth, “Come on baby. Give me that thick fucking cock.”

“Like this?” He said in surprise.

Addison grinned up at him from her position, “Trust me, Dean. You’ll never be the same after today.”

With a slight hesitancy, Dean lowered his hardness into her waiting mouth slowly, bracing himself on the bed on either side of her body. Dean shuddered as she mewled around her mouthful. He stopped when he felt he was already in too far and slowly pulled out again before thrusting back in gently. 

Addison let him go with a pop, and raised her eyebrows at him, “Stop being greedy and give it to me.”

Dean let out a small huff of disbelief, “I don’t wanna hurt you.”

Addison removed her glasses and handed them to him as she motioned for him to place them on the side of the bed, “Trust me. I’ll pat you on the leg if I feel uncomfortable.” She winked at him, “But I won’t.”

Dean blinked and shrugged, “Uh, okay.”

Once more, he leaned his cock into her mouth and followed her guidance as she pulled on the back of his leg toward her to get him deeper, “Fuck.” He gasped out.

She was sucking him so deep he could feel it in his toes.

“Mmmmmm…” Addison hummed around his cock and swallowed him down until he could practically see himself protruding from her neck.

“Oh my god.” The heat from her mouth, combined with her tight swallows was making his balls tingle in warning. 

He moved to pull out but Addison pushed him back in. He tried again and she pushed him back moaning around him. Eventually he gave up trying to stop the madness and instead started to thrust into her mouth, much to her delight. 

It was so fucking good. So sexy. So raw. Her throat taking him so well as he grunted with each thrust of his hips.

Dean watched as her thighs starting squeezing together and he reached down with one hand and rubbed against her clit as he thrust into her mouth, harsh gasps leaving his lips. She moaned again before starting to lift her hips in time with his motions. 

She popped him out of her mouth, saliva stringing from her lips and let out a whine before reaching underneath his cock and tonguing his sack, popping them gently in her mouth as she stroked at his cock.

Dean squeezed his eyes shut and tried deep breathing techniques to stop the impending orgasm that was threatening its way out.

Addison gave him one last suck on his balls before turning over on the bed and gulping down his cock and popping it out of her mouth again, “Talk to me, Dean.” She said licking at his tip, “Tell me how good it feels when I suck your cock. Tell me what you’re going to do to me.”

Dean blinked down at her, “Ummmm, you want me to what?”

She rolled her eyes up to him, and shoved him all the way down her throat making him shudder, before she released him, “Tell me you’re gonna fuck me until I can’t talk, Dean. Tell me my pussy tasted delicious.”

“You, uh, want me to talk dirty to you?” Dean said with apprehension.

With a swirl of her tongue around his tip, she hummed, “Fuck yeah. Women love to be told how good you’re gonna give it to them.”

Dean cleared his throat, “I, uh, don’t normally go into detail, I mean, I-.”

Addison stopped what she was doing and got up on her knees, throwing her arms around his neck before licking and biting his neck, making things inside of him tighten further, “Trust me, Dean. It’s fucking hot.” 

“I guess I, uh, don’t want to sound stupid.”

Sliding her tongue down his chest and swirling it over a nipple, Addison smiled up at him, “Do you want to fuck my pussy, Dean? Do you want to feel how warm and wet it is?” She grabbed at his dick, “With this beautiful cock that fits so good down my throat?”

Dean groaned and gave in as lust clouded his mind even more, “Fuck yes. Wanna fuck you so bad.”

“How bad do you want it, Dean?”

He grabbed her hips and threw her down onto the bed before lowering his body over hers, “Gonna fuck you raw, baby. Gonna make you scream.”

Addison’s eyes rolled and she bit her bottom lip as her hips canted upwards. She reached over to the bedside table drawer and pulled out a condom, handing it to him, “So do it.”

Quickly he rolled on the condom and threw one of her legs over his shoulder, opening her up to him, “Such a pretty pussy.” He rubbed at her clit with a thumb watching as she started to breathe erratically, “Is it ready to take me or do you need more time?”

“Now. Fuck me now. I want it so bad.”

He leaned down bringing her knee to her chest hovering his mouth over her lips, “I don’t know. I don’t think you want it bad enough.” He rubbed the tip of his cock over her clit. Once, twice, three times.

Addison whined and licked at his lips, “Oh God, yes I do.”

The power trip was making Dean a little dizzy as his heart pounded in his chest, “Hmmm, you sure?” He rubbed himself even harder against her, her slick making him slide easily.

She moaned and lifted her hips, trying to get him to slip inside, “Please. Please…”

He was almost tempted to make her beg even more, but her pleas made his stomach burn with tension. He braced himself more firmly, “Since you asked so nicely.” He entered her in one smooth stroke and moaned as she immediately started tightening around him, and he whispered against her lips, “Fuck, you feel good. So tight. Gonna make me come so hard.”

Addison started moaning in earnest and moved her other leg on top of his shoulder, making them both gasp at the depth he was able to stroke into her, “Shit! Yes! Faster, please. You’re fucking me so good. I’m gonna come.”

With a grunt, Dean placed his hands on either side of her head and started pounding into her, the speed making his eyes roll into the back of his head as she screamed, the vise grip her pussy had over him as she orgasmed making him unable to stop himself from exploding into the condom as he moaned deep in his chest, “Fuck, yeah!”

For the next four hours, Addison made the filthiest things come out of his mouth. Things he didn’t even plan on doing but she liked hearing him say them anyway.

By the time he walked back to his car, he could feel the blush rising in remembrance and he chuckled to himself as he rubbed his hands over his face and grinned.

Always the quiet ones.

*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*

Dean was twenty-four when he first got his heart broken.


	5. Chapter 5

**Summary for the Chapter:**

> Dean Winchester has reached a point in his life where he doesn’t have many firsts left to fulfill. Except maybe falling in love. This is the story of how he got there.

**Notes for the Chapter:**

> Soooo, this is pretty long but I felt it needed more details than just Dean meets cute girl/Dean sleeps with cute girl especially since in the show they put it out there that Dean cared deeply about this particular girl. So folks, I give you the scenes you probably never wanted but I needed to write. I present to you Dean x Cassie. 
> 
> Oh and by the way, the next part, Chapter 6, is the last chapter before Dean meets reader. 
> 
> Please note, this is unbeta’d. Any and all grammatical errors are mine. (And I’m sure there are PLENTY. :))

Dean was twenty-four when he first got his heart broken.

He had always loved visiting college campus’.  Especially in the springtime.  The short skirts.  The tank tops.  The sparkling smiles of the girls as they ran their gaze over him and gave him flirtatious eyes. 

It was a miracle he ever got anything done when he was working a case near one.  

But then he quickly learned that while the easy ones were, well, _easy,_ it didn’t make them anyone he could see past a quick night together followed by moving on without so much as a glance back. 

And if you asked his father that was exactly the way it should be.

But then, Dean met _her_. 

The girl with the mocha skin and the thick curly hair and the attitude to match.  And God she made things inside him tighten that had nothing and everything to do with sex.

Dean was with his dad on campus, posing as a junior reporter to his senior one while John was interviewing a professor about a dead student that had been found with his throat ripped out, when he saw her. 

She was reading a sheaf of papers in her hand, her eyebrows drawn together as she read through the text.  She stopped in the middle of the campus road and rolled her eyes at what she read and threw her hand up in exasperation

Dean heard the rumble of his father’s questions to the professor and gave small reassuring smiles at all the right times as he pretended to write down notes but his eyes and attention kept straying back to her.

She drew her phone out while she bit her bottom lip and tapped her foot, “Sal.  Yeah, it’s Cassie.  Can you please explain to me this drivel you want me to publish in the schools paper?”  She waited a beat as the person answered, “Yes!  Drivel! As in nonsense, twaddle and every other synonym that’s nicer than the word _garbage_.  Were you high when you wrote this?  Oh, please don’t get offended on me.  You and I both know better.  What do I want?  It’s not what I want, it’s what you’re gonna do.  You’re gonna give me an article that I can actually publish and not make me look like a moron Editor who doesn’t proofread her staff’s work, capisce?”  She smiled, “That’s what I like to hear, Sal.  Talk to ya later.”  She hung up and started rustling through her bag.

Dean bit his lip to stop from laughing at the poor shmuck that was on the receiving end of her wrath.  As if she could feel his stare, Cassie looked up and into Dean’s gaze and he gave her his lazy smile.

She stared back at him for the briefest of seconds before pursing her lips and giving him a look that he guessed would wither weaker men, “Is there something I can help you with?”

The attitude in her voice took him aback and his smile abruptly dropped, “Why am I afraid to answer that question?”

The professor and his father both turned to see who Dean was talking to and the professor perked up, “Oh!  Cassie!  Perfect timing.”  He turned back to John, “She’s the Editor-In-Chief of our school paper.  Cassie, these gentleman are here from the local paper and they have some questions about the terrible death of Simon Delanos.  I know you wrote that wonderful article about him.  Maybe you can shed some light for them, hmmm?”

Cassie gave the professor a tight smile and turned back to the father and son, “Local paper huh?  Which one if you don’t mind me asking?”

John sent her a grin, “The Sun.”

Cassie raised her eyebrows, clearly unimpressed by the two men, “Well, I’m on a little bit of a deadline but I can chat for a couple of minutes.  What would you like to know?”

Dean stood by and listened as his father questioned Cassie and couldn’t help but stare at her petite but tight frame.  Her curly hair was wild around her head and her deep brown almond shaped eyes glittered with intelligence as she deliberately avoided Dean’s gaze.  She answered his father’s questions, clearly, concisely and without any extra hoopla.

She made things in Dean’s lower belly flutter and he both liked and hated it.   

He desperately wanted to see her smile.  The real one.  Not the strained, you’re bothering me but I’m trying to be polite tight lipped smile she gave them earlier.    

Cassie looked down at her watch and grimaced, “Well, gentleman, I hope I was able to help with the article, but I have to run.  Have a bunch of articles of my own to look through.”

John reached a hand out and grasped hers, “Totally understand.  Thanks for the time.”

Dean spoke up, “Wait, uh, if we have any more questions, where is the best place to reach you?”

Cassie gave him a skeptical look.

He shrugged trying to make it look casual as he smiled cajolingly, “Hey, you never know when having a contact at the local paper could come in handy after graduating.”

With a purse of her lips at the blatant bribe, Cassie wrote down her number on a piece of paper and bypassed the hand Dean reached out with and instead handed it to his father, “I doubt I could be of any more help, but, just in case.  Gotta run.” 

And with that she hurriedly moved down the campus walkway and into one of the buildings.

Be still his heart.

Dean spent the rest of the day looking at the paper he had filched from his father’s pocket. 

Should he call? 

Shouldn’t he?

What would be his cover story?

Should he just be honest about his intentions?

Why was he second, third and fourth guessing himself? 

Dean rubbed his thumb and forefinger over his eyes before letting out a frustrated growl, making his father look up from his research with a frown.

“What’s the matter?  What’s with all the grumbling?”

Dean shook his head and closed the book in front of him, “Nothing, Dad.  I think I just need a break is all.  Gonna go take a walk.”

His father’s frown deepened but he nodded, “All right.  Just be careful.  We’re still trying to figure this one out.  There’s already three people dead including the one at the campus.”

Dean nodded before walking out the motel’s door. 

The spring night air hit Dean’s face and he inhaled letting the scent of freshly mown grass and flowers hit his nose.  They had opted to stay in town next to the latest murder and he was only a few blocks away from the main campus.  In the daytime, the houses lining the streets leading to the campus looked like regular homes.  At night however, the homes lit up and he could clearly see that some of those buildings were Sorority and Frat houses. There were students milling around one particular house with a big Alpha Phi sign hanging off the front entrance.  Music was coming from inside and he could hear cheers coming from the back of it.  Laughter rolled through the air with a lightness that he hadn’t felt in years. 

Knowing the monsters that bumped in the night were real kind of put a damper on your outlook on life.

For the briefest of moments he wondered if Sam was living this kind of life.  Laughing with his friends. His biggest worry being about an exam. Having a pretty girl by his side for more than just a day or a weekend.

Dean smiled.  If his baby brother was living the apple pie life, then he hoped he was embracing each moment.  If there was anyone in this world who deserved it, who had worked hard for it, it was his little brother.

And Dean would fight to keep him out of his world for as long as he could.

A bump into his shoulder interrupted his musings.

“Oh!  I’m so sorry!”

Dean turned and was met with two girls.  The one who had bumped into him was a blonde girl wearing a v-neck body suit tucked into short-shorts.  He was pretty sure if she bent over he’d be able to see her business.

It was warm out but it wasn’t _that_ warm out.

Dean cleared his throat, “No worries.”

The blonde looked at him, her gaze going over his features as her blue eyes turned flirty, “Hey, aren’t you from Phi Kappa Tau?”

“Uh, no.  I’m, uh, just visiting.”

The brunette that was with her, dressed slightly more conservatively, spoke up, “Well, why don’t you just visit with us at that party over there?”

Dean looked at the house skeptically, “Do they have booze?”

Both of the girls rolled their eyes and replied, “Duh.”

Ah.  College girls. 

With a shrug, Dean followed them into the house, trying to keep up with their questions as he looked around. 

It took five minutes for the blonde to get him a drink.  It took thirty for her to start getting tipsy on the jungle juice.  Another thirty minutes later, he was desperately trying to evade her grabs around his ass and his crotch. 

He didn’t do drunk and disorderly females.  That’s how you got yourself arrested.

Instead, he finally found the girl she had arrived with and shoved her to her friend, “I’ll be right back.”  He said in her ear before turning around with an exasperated huff and wide eyes.

Only to be met with a set of amused almond shaped ones.

“Cassie!”  He said with an uncomfortable gulp, as he took in her appearance.  She was dressed casually, wearing a deep purple silky tank top over a pair of hip hugging jeans and heeled sandals; her hair wild around her face.

And again he was struck with that feeling in his gut that didn’t seem to want to go away.

“Uh, hi.”

“I see Bouncy Barbara got her paws on you.”

“Bounce this bitch!”  Barbara slurred.

Cassie let out a loud sarcastic laugh, “Aww, isn’t she adorable?”

The brunette with her rolled her eyes and pulled on her arm, ignoring Cassie and Dean, “Come on, Barbara.  I gotta pee.”  With that, they both stumbled away.

Dean raised an eyebrow at Cassie, “Bouncy Barbara?”

Cassie smirked, “Yeah, I like to tell myself it’s because she bounces from guy to guy, but, since it was some Frat guys that gave her the nickname, I’m pretty sure it has more of a sexual innuendo that I’m not trying to think too hard on.”

 Dean pursed his lips as if in thought, “Yeah, I can see a couple of different scenarios making that happen.”

Cassie rolled her eyes good naturedly, “Gross.”

As Dean smiled down at her, he realized just how close to him she was standing and just how smooth her skin was.  There was a soft scent coming off her that was making his stomach rumble and he had to clear his throat before speaking, “Uh, so what are you doing here?  This doesn’t really seem like your kind of scene.”

With a raise of her eyebrows, Cassie crossed her arms over her chest, “Oh yeah?  And why’s that?”

Dean shrugged, “I dunno.  You just seem….”

“Boring?”

He leaned back in true shock, “No!  No, not at all.  I almost feel like you have like a laundry list of things more important to do.  Like maybe train people on how to wither men with verbal judo and a cold stare.”

Cassie bit her lip in an attempt to stop a smile, “Well, believe it or not, I’m a part of this Sorority and I have to make an appearance every now and then at these parties.”

“No way!  No, you’re not.”

Cassie sighed and continued trying to bite back her smile, “Yeah, well, graduate schools love to see this stuff on an application and having these kind of connections after graduation, because, you know, ‘sisterhood’, could help move along a career, so, yeah, here I am.”

“Ha!  I knew there were ulterior motives.”

“Well, there definitely were at first.  But, these girls aren’t that bad.  And when they aren’t partying, they really do some good things for the community.  And _that_ I like.”

Dean found he couldn’t help but step a little closer to her, “Oh, yeah?  Like what?”

Cassie opened her mouth to answer and then abruptly shut it, while she looked up at him suspiciously, “Do you really want to hear this?”

With a shrug, Dean looked around and then back at her, “You’re the most interesting thing in this room right now, so yeah?”

“Even more interesting than that guy currently trying to do a keg stand in a squirrel costume?”

He continued to stare down into her eyes, not taking the bait, and said lowly, “Absolutely.”

And then Dean’s world turned upside down and right side up because he finally got what he had been waiting hours for. 

Cassie smiled.

And it made the rumble in his stomach ignite.

*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*

It took three days of phone calls, randomly showing up at the campus and the schools newspaper office to get Cassie to agree to out with him on a real date and even then she fought him on the venue.  Dean wanted to take her to a nice restaurant but Cassie insisted on picking out the place herself.

“If I’m gonna be forced to sit across from you for a meal, then it’s gonna be a damn good one.”  She told him on the phone.

And that’s how Dean found himself outside of a hole in the wall on some random street about a half hour from campus, “Uh, you sure this is the place?”

Cassie smirked at him, “Yep.  What’s the matter Dean?  Nervous?”

Dean scoffed, “Who me? No!”  He looked at the entrance again, “It’s just, uh, I don’t know how this is better than the Italian restaurant a block away from the college.”

Cassie did the one thing that seemed to always get him to shut up.

She smiled.

And his resolve melted and he easily followed her to the doorway and opened it for her.

 “Trust me.”  She said, “This right here?  Is the best barbecue joint in existence.”

And it was. 

The place was truly a hidden gem with a small restaurant area that opened up to a huge back space that took Dean a minute to realize was actually outside but was covered with heavy duty tarp like walls.  Every few feet there were standing heaters warming the space up and a long bar along the back with a pretty thirty something brunette bartender making complicated drinks as she smiled at the patrons.  Low rock music was playing out of hidden speakers and the lighting was soft with an intimate feel.    

Cassie led him over to a back table set for four in a corner close to the bar and indicated for Dean to sit, “I’ll be right back.  I’m just gonna say hello to my friend Trina.”

Cassie walked over to the brunette bartender with a smile and she stopped what she was doing to give Cassie a big hug over the bar, “Cassie!  Haven’t seen you in a couple months.  How are you, doll?

“I’m good, Trina.  Just craving some good food.  I set myself up at my usual table if you don’t mind.”

Trina slid her eyes over to the corner table where a waitress was placing two glasses of water on the table in front of Dean and her eyes widened appreciatively before turning back to Cassie and saying loud enough for Dean to hear, “Oh, honey, as long as I get to look at that all night you can sit wherever you want.”

Dean smiled as Cassie smirked and rolled her eyes, “Oh please, Trina.  His head is already big enough.  Please don’t give it even more reason to swell.” 

“Mmmhmm.  I’m sure there are plenty of things big enough on that one.”

Dean choked on the water he had sipped and quickly brought a napkin to his mouth.

Cassie bit back a smile, “I wouldn’t know.”

Trina raised an eyebrow, “And what the fuck you waitin’ on, honey?  A gilded invitation with a dick embossed on it?”

Cassie finally looked a little embarrassed as she lowered her voice, “It’s technically only our first date.”

“And?”  Trina deadpanned.  At Cassie’s exasperated sigh she continued, her voice lowered as well, “Men like that don’t stick around for long, honey.  You better ride that man and put him away wet so that you can send him on his merry way.  Don’t be falling in love, honey.  Just fall on that dick.  Ya heard?”

“Holy shit, Trina.”  Cassie said in exasperation.  “You are the fucking worst.”

With a shrug Trina smiled at the next customer and indicated to them to give her a second, “Yep.  And I’m right.  Enjoy that man.”  She looked past Cassie and stared at Dean again, “For the both of us.  Yum.”

With a small smile and a final roll of her eyes, Cassie made her way back to a shit eating grin, “Don’t start.”  She said to Dean as she sat across from him.

Dean took another gulp of water, “Don’t know what you mean.”  He sat back and put an arm around the empty chair next to him and smiled at her, “But I gotta say.  Never had to send an invitation out before.  But if that’s how you roll….”

Cassie finally let out the laugh she had been holding back at the bar and the sound echoed in Dean’s ears. 

Beautiful.

*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

Dean didn’t know if it was Trina’s advice or the three Hennessey Mojitos Cassie had at Trina’s insistence, but she was smiling more than he had ever seen and currently giggling her way out of the restaurant to Dean’s car.

It had been an actual date.  They had talked, laughed and he had heard what she wanted to do with her life.  She had such ambition.  Goals.  And she wasn’t afraid to go after them.  No matter who got in her way.

And when he was with her, Dean felt a little of the raincloud over his head clear.

He actually felt…happy. 

Cassie turned and leaned against the passenger side door to face him.

“Sooooo?  What did you think?”  Cassie cajoled.

Dean put his hands in his pockets and smiled as he looked down into her face, “About what?”

“The restaurant!”

Dean shrugged, “The food was delicious.  But the company was even better.”  Dean leaned down and he heard her breath catch before he kissed Cassie chastely on the cheek and straightened up, “I had a great time, Cassie.”

Cassie took a deep breath and it may have been wishful thinking on his part, but he could swear she looked a little disappointed, “So did I, Dean.  You…you’re not what I expected.”

“Oh, yeah. How’s that?”

Cassie shrugged and looked away before bringing her eyes back to his, “I don’t know.  I guess I expected you to try and make a move four days ago at that sorority party and when you didn’t and then actually called the next day and started asking for an actual date and you weren’t obnoxious about it, I dunno…”  She rambled before letting her words fade into the air between them.

When Dean smirked at her, she rolled her eyes, “I mean don’t get me wrong you _are_ obnoxious.  It’s easy to tell you love the shit outta yourself but…..I don’t know.  You…you’re just not the guy I initially thought you were, is all.”

Dean reached out and rolled one of her errant curls around his finger before letting it bounce back into the wild mane and stared into her eyes, “I won’t lie.  I’m usually a pounce first ask questions later kinda guy but…you…”  He stepped closer and leaned against the side of the car next to her, until he could feel the heat from her body caressing against his shirt, as he turned his head and looked down at her, “You’re different.”  He licked his lips as he watched her eyes follow the motion, “Besides, I was afraid you’d chop me in the throat if I tried something.”

Cassie let out an indignant sound, “I am not _that_ bad.”

His mouth quirked up, “Didn’t say it was bad.  Just said I was afraid.  Just like I kinda am now.”

Her eyes searched his as the shaky puffs from her mouth hit his lips, “Of what?” She whispered.

Instead of answering, Dean raised his hand and carefully palmed her cheek as he caressed her skin with his thumb, “Can I…..can I kiss you?”

Cassie swallowed thickly as she nodded and closed her eyes as Dean brought her mouth to his.  The first taste of her lips made him hum deep in his throat and while he was careful to take it slow, Cassie didn’t seem to want to stay on the same track as she opened her mouth under his and deepened the kiss.  The first swipe of her tongue made his stomach clench and when he tangled his tongue around hers, he reached up and grasped her head in both of his hands and worshipped her mouth as a buzzing filled his ears. 

The kiss seemed to last forever and not long enough and when he released her mouth he laid his forehead against hers and breathed heavily, “That was….just…wow.”

Cassie’s eyes closed briefly at his words before she ran her fingers through the short strands of his hair at the back of his head, “Take me home.”

His shoulders slumped in slight disappointment but he nodded and started to step back, “Sure.”

Her hands came back up and grabbed at his face before she slotted her mouth against his, kissed him breathless and released him, “I meant, take me home and stay there with me.”

With a harsh swallow as his heart leaped in his chest, Dean nodded again and reached down to open the passenger door for her.

The drive back to her small off campus apartment was a blur and he couldn’t stop the harsh pounding of his heart.  At a red light, he slid his hand over to hers and entwined his long fingers in between her own before bringing her hand up to his lips and placing a soft kiss to the top of it.

He watched as she brought their entwined hands to her own mouth and kissed the tips of his fingers with a gentleness that made his stomach drop.  The harsh sound of a horn behind them made him jump out of his stupor as he made note of the now green light and continued on to her house.

Dean had expected it to be good.  He had expected it to be passionate.  What he hadn’t expected was for it to make him never want to leave.

He spent a half hour on her bed just worshipping her mouth and running his hands over her clothed body, listening for the hitches in her breath depending on where he touched her.  And when he finally ran his hand over her jean covered core, he hadn’t expected to want to slow down instead of dragging her pants down her legs.  He hadn’t expected his hands to work their way back to her face and hold it in his palms as he licked his way into her mouth instead of licking his way into her core.

He definitely hadn’t expected Cassie to make the first move and pull her shirt up and over her head before reaching for the bottom of his gray Henley and whipping it off of his body.

And when her mouth dragged from his collarbone to his chest to his belly button, licking along the edge of his jeans, he hadn’t expected the thundering of his heart to match the moan from his chest as his cock swelled to uncomfortable proportions.

Cassie quirked her eyebrow as if asking for permission as her hand hovered over his fly and he nodded jerkily. With a quick flick of her wrist, the button on his jeans popped open and she was carefully lowering the zipper before she helped him shimmy out of his jeans.  The clear outline of his erection was prominent inside his black boxer briefs and when Cassie lowered her head and mouthed along the ridges through his underwear, Dean’s breath caught and his hips involuntarily rose and he let out a soft groan.

“Wait…Cassie…”

Dean quickly sat up and brought her mouth back to his, ran his hands over her back and quickly flicked open her bra.  He pulled back from the kiss and slowly slid the straps down her shoulders, his fingers caressing against the skin of her arms as he revealed her breasts to him for the first time.

His eyes probably stayed glued to her chest for far longer than recommended but he couldn’t help the appreciative gaze that he gave her before letting out a shaky breath, “You’re beautiful.”

Cassie bit her lip and looked uncharacteristically shy under his gaze before standing off of the bed and pulling off her jeans, leaving her black lace panties on. 

Before she could make another move, Dean swung his legs off of the end of the bed and reached out to her, smoothing his hands over her bare stomach before grabbing her around her waist and lifting her to straddle him.  When her core bumped against his throbbing cock, they both groaned and moved into the friction as they crashed their mouths against one another, tongues flashing in the air as they swallowed each other’s deep groans.

Cassie crested her hips over his cock and pressed down harder through her panties making his underwear damp with her arousal.  Dean reached down and grazed his fingers over the outside of underwear and moaned when he felt how soaked she was as her underwear glided over folds.

“Cassie….I gotta touch you.”  He breathed, as if asking for permission to touch her bare.

She nipped her way down to his neck and bit at his pulse point before reaching down and bringing his hand inside her panties, moaning when he slid two fingers over her clit and pressed down hard, “Again…” She moaned holding her hand over his and pressing him where she wanted it most, helping his fingers slide up and down her soaking pussy before he finally inserted his fingers into her hole “Yes…just like that.”

Dean’s hips jerked up at the breathy sounds she was making, his cock aching and leaking into his boxers.  He mouthed her neck and slid down her shoulders to her chest before licking a nipple into his mouth and sucking until it hardened into a peak, “Cassie,” He groaned around her breast, “I need to taste you.”

Without waiting for a response, he flipped her onto her back and quickly slid her lace panties down her legs.  Her wet core glistened back at him and he hummed, looking up at her as he licked up one of her thighs. 

Her eyes glittered back at him and she bit her bottom lip as her chest rose and fell with her heavy breaths, “Dean….please…I….”

“What, Baby?”

“Please….just….”

Dean bit his bottom lip into his mouth before sliding his tongue the rest of the way up her thigh and into her core with one stroke, humming in satisfaction as she cried out and placed her hand in his hair, her hips jerking up, “Oh, God.”

Her body let out more slick into his mouth and he moaned as he sucked her clit in between his lips, before flicking it with his tongue.  Cassie let out a loud whine and moved her hips in time to the strokes of his licks.

Holding her hips down with one hand, Dean smoothly entered her core with two fingers as he continued to suck on her clit.  When he hooked his fingers just so and heard her gasp into the air, he knew he had found her sweet spot and quickly massaged the area.

“Yessss, just like that.”  Cassie gasped, her fingers of one hand hooked into the short strands of his hair and pulled roughly making him growl and thrust his cock into the bedspread underneath him.

“Fuck, Cassie.”  He said as he laved at her clit,   “You gonna come for me, baby?”

“Oh, God…ohgodohgodohgod.” 

Her legs tensed around his head and Dean rubbed harder against the rough spot inside of her.  When she threw her head back and let out a moan of completion, Dean moaned in unison and eagerly lapped up her slick.  He pulled his fingers out of her slowly letting her ride out the orgasm before bringing his fingers to his mouth and sucking off the remnants of her.

Delicious.

He hovered over her, his eyes flicking everywhere, watching her heavy breaths, memorizing the way her full lips were parted, the look of lazy satisfaction as she came down and the small almost embarrassed smile she sent his way.

“Well, you are almost too good at that.”  She said with a slight laugh.

He smiled and braced himself on his forearms as he brought his mouth back to hers and worshipped her lips with slow, sensuous kisses. 

Soon, Cassie was pushing at his boxer briefs and helping him to slide them down his legs, before pulling out a condom from her bedside drawer.  She sat up and he sat back on his legs, his cock throbbing as she grasped it in her hand and stroked him from root to tip and back again, her hand picking up the pace of her strokes when she heard him let out a low moan and start to move his hips slightly to her rhythm.  Drops of pre-come leaked down the sides of his cock and he could feel the tingling warning him that he was cutting it close.  

Staying her hand, Dean reached for the condom and quickly ripped open the package and rolled it on.  Cassie lay back down and looked up at him, her eyes softer than he’d ever seen them, and he ran a finger from her arched eyebrow down her cheek to the softness of her lips before leaning down and kissing her with gentleness that he couldn’t remember ever doing before.  He hovered at her entrance and pulled away from her lips, wanting to see into her eyes as he pushed into her core, lips parting slightly at the searing heat of her body.

She was perfect.  And for the first time he felt his heart clench in fear. 

Eventually he’d have to leave her.

God help him, but already he didn’t want to.

Cassie lifted her legs and brought her knees to his sides, effectively bringing him deep and his eyes crossed.  He pushed all other thought to the back of his mind and began thrusting in earnest as Cassie moaned into his ear and stroked up his back, her nails digging into the muscles of his shoulders as she desperately met his strokes.

A haze fell over him and he watched as Cassie fell apart underneath him, screaming his name.

And before he let go, he realized for the first time in his life, Dean Winchester had just made love to a woman.

*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*

The next morning, the sunlight shining in through a window woke Dean as it pressed against his eyelids.  He winced against the brightness before he turned his head and looked over at the smooth shoulder next to him, errant curls brushing against it, her face turned away from him.  He let a small smile slide across his mouth as he watched the quiet breaths lift her chest.

He was about to reach over and kiss her awake when a low buzzing sound caught his attention.  He looked around momentarily confused until he realized with a start it was his cell phone. 

And only one person would be calling him at this early hour.

His father.

Shit.

As quietly as he could, he padded over to his discarded boxer briefs and pulled them on as he looked for his jeans, finding them on the other side of the room.  The buzzing sound momentarily stopped before immediately starting up again and Dean felt a small smidge of panic lay low in his stomach as he finally grabbed up the jeans and pulled out his phone, flicking it open just as it was going to switch over to voicemail.

“Hel-.”

“Boy! I have been calling you for hours.  Where the hell are you?  I have a lead on the case and I need you as backup.  Now get your dick outta whatever hidey hole it slithered into and get your ass back to the hotel.  Now!”

Dean took a deep breath and considered arguing but instead muttered a “Yessir,” into the phone and winced at the loud click of his father hanging up.

“Everything okay?”

Dean turned to see Cassie sitting up in the bed holding the sheet to her breasts as she rubbed her sleepy eyes.

God, she was beautiful and strong and everything he wanted and needed right now.

But he had a job to do. 

“Yeah.  Yeah.  But I, uh, I have to go.”  He said briskly as he pulled his jeans up his legs and looked around for his socks and boots.

Cassie pointed over to where his socks were sticking out of his boots in another corner of the room and gave him a disappointed but guarded look, “Is this where you’ll tell me, you’ll call me but never will?”

Dean immediately stopped in his tracks and made his way back to her side on the bed and sat down before bringing her mouth to his for a soft kiss and releasing her all too soon, “No.  I don’t want to go.  But my, uh, work just called and they’re sending me somewhere for my assignment.”  He kissed the corner of her mouth again, “I don’t have a choice.”

Cassie leaned into his kisses, and placed her chin on his shoulder, “When will you be back?”

Dean looked all over her face and tried to memorize all the little details, “As soon as I can.  I’ll call you tonight.”

She nodded but as he tried to stand she grabbed his hand and brought him back down to her, her eyes wide with an unspoken emotion, “Dean, I just want you to know….I, uh, last night, it meant a lot to me.  It wasn’t just a one time thing for me.”

Dean desperately wanted to tell her he felt the same.  Wanted to make love to her all over again, whispering promises of forever against her skin.  But the lord only knew what he was going to be facing today.

And that scared him.

For the first time in a long time, he was scared of what they would find because he was scared he wouldn’t come back.

So, instead of telling her what he really wanted to, he grabbed her face and gave her one last kiss.  He quickly finished dressing and gave her a wink and a smile as he let himself out of her apartment.

~**~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*

The lead his father had didn’t amount to anything, much to his father’s frustration. 

Which meant, back to researching, back to interviewing and back to the coroner’s office to look at the latest victim.     

But that also meant more time with Cassie.  And while Dean hated that another life was lost, he couldn’t say that he was unhappy to be staying longer.

Especially, when he saw her smile when he came back that night to her apartment.

His father and he stayed in that town for a month and a half.  While they struggled during the day to figure out what was killing these people, he spent the nights bathing in Cassie’s smiles.

Until the questions started.

How was his article coming? Why did his supervisor call him so much?  What was it that he was looking for?

And then began the tension once those questions couldn’t be answered properly, Cassie’s eyebrows rising in disbelief when he stuttered out vague answers.  Lucky for him, that angry tension almost always lead to sexual tension and before either of them could say another angry word to one another, Dean had Cassie laid out on her bed while he worshipped every exposed part of her skin.  His tongue digging deep inside her soaking pussy as he rubbed harshly at her clit, chasing those sweet, sweet sounds she made when he ate at her like this.  The desperate moans that made him so horny he would reach down and stroke himself, grabbing at his sack as he desperately tried to ease some of the ache she produced deep inside of him.    

The night his father broke the case realizing a pair of Vetala was to blame, Dean had to leave Cassie abruptly and go help his father gank them.  It hadn’t been easy and when all was said and done, he was left with what he hoped was just bruised ribs and his father’s eye was swollen shut.

But they had been successful.

Only, there had been no time to celebrate as a hunter friend of John’s called when they were on their way back to the motel and needed help on a case two states away.

Dean’s heart dropped when he heard his Dad tell his buddy they would be leaving as soon as they packed the rest of their shit.

And now the time Dean had been dreading for weeks was finally here.

It was time to say goodbye.

Dean somehow convinced his father that he needed to rest for at least a couple of hours and ice his eye before it got any worse.  Lucky for him, the minute his father hit the bed he was out like a light and Dean was slipping out the door to his car and on the way back to Cassie’s apartment.

The whole way there he mentally prepared himself to tell her that he was being relocated to another state.  Or that his job was putting him on an assignment with no known end.  But in his mind, he could hear her say that they could still make it work.  Her stubborn nature coming out and demanding details. Answers.

And then what?

He didn’t want to lie anymore.  He didn’t want to leave her.  But he had to make her understand why he had to.  Why it was important that he continue doing this. 

And above all he didn’t want to lose her.

He refused to think on what that tight feeling in his chest was or what the knot the formed in his stomach when he thought about leaving her meant.

Because if he thought any harder on it, he’d have to explore what these feelings were and Dean Winchester didn’t do those kinds of feelings….right?

Right?

Shit.

Somewhere between leaving the motel and getting to Cassie’s Dean made a life altering decision.  He was going to tell Cassie the truth.  He’d still have to leave but at the very least he could come back when he could.

He wouldn’t have to let her go.

Ignoring the tremors in his hand as he raised it to ring Cassie’s bell, Dean held his breath until she opened the door with a wide smile.

“Hey!”  She reached out to him and pulled him into a hug, pulling back in concern when he grunted in pain as she inadvertently squeezed his ribs, “What’s the matter?  You okay?”

Dean swallowed hard and pulled her into a rough kiss before letting her go and resting his head on hers, “We….we need to talk.”

Cassie pulled away from him, her now wary eyes scrunched in confusion, “Dean, what’s going on?”

Dean pulled her into her living room and sat her down on the couch as he sat down on her coffee table in front of her, his hands folded nervously in front of him, “Okay, so uh, I have to leave.  In a few hours.  And I don’t know when I’m going to be back.”

Cassie sat up and blinked, “Oh….why?  Where are you going?  Is it your job?”

Dean let out a small nervous laugh, “Yeah.  Umm…yeah but my job……my job is not what I’ve been telling you.”

At that Cassie’s shoulders tightened, “What do you mean?”

Dean reached up and smoothed out the angry lines of her eyebrows before bringing her mouth to his, needing to feel her.  Needing to feel the intoxicating emotions she arose in him giving him the confidence to tell her this next part.  To assure him that he was doing the right thing.

Releasing her mouth slowly, he sat back and took a deep breath, “Cassie, my job….what I do….I….”

Cassie grabbed onto his hand, “Dean, talk to me.  You can tell me.”

He nodded and gave her a small tremulous smile, “I’m a Hunter.  My job is to kill things that go bump in the night.  Monsters.  Before I came here I went with my father, the guy you know as my supervisor, John, to kill something called a Vetala.  It’s what’s been murdering all those people in town.  And I have to leave in a few hours to help some other hunters on another case.”

Cassie’s hand released Dean’s and she sat back, her eyebrows now scrunched in confusion and not a little bit of anger, “Dean…..what you’re saying is making no sense.”

“I know.  But it’s the truth.  And….and I’ve never told anyone that before.  I mean I’ve never told anyone I’ve ever been with.  But the reason I’m tell-.”

Cassie raised a hand to stop him, and he noticed it was trembling, “Dean, if you need to leave that’s fine but you don’t have to come up with these crazy stories.  It’s not necessary.”  She stood up and let out a scoff, “This is one for the books.” She muttered to herself.

Dean stood up as well, his eyes wide in panic, “Cassie, please.  I’m telling you the truth.  I wish I could stay but I have to help my dad.  He needs me right now.”

When he reached out to her, she slapped his hand away, “Don’t touch me, Dean.” She said angrily as she pointed an accusing finger at him, “The things I felt for you…I…thought you felt the same.  I thought….”  Her eyes filled with tears and he could see her struggling not to let them fall.

Dean was frantic now his breath coming in gasps, “Cassie, baby, please, you’ve gotta believe me.  I want to stay but I can’t.”

Cassie’s lips pursed and he saw her swallow thickly as an errant tear slid down her cheek before she roughly brushed it away, “Right.  Because you have to go fight monsters.”  She scoffed again, before her face hardened, “Get out.”

Dean’s face fell and the breath knocked out of him, “Wh-what?”

“I said get out!”  She screamed.

Dean stood there blinking at her as the pressure in his chest rose into his throat and he felt his mind blank out at her rejection. 

She didn’t believe him.

For the first time in his life, he was honest about who he was and what he did and she wouldn’t even let him talk.

Cassie didn’t believe him. 

As something inside of him shattered, Dean’s shoulders straightened out and his face hardened and he put on a nonchalant air as he pursed his lips, “Fine.  Just remember who walked away from whom.”

With one last lingering look at her angry eyes, he turned on his booted feet and made his way to the door, slamming it behind him.

And if his chin trembled when he got behind the wheel it was because he was so angry.  And if his eyes burned and throbbed the whole way back to the motel it was because he was tired. 

But when he laid his head on his pillow that night, groaning at the pain in his ribs, listening to his father’s soft snores, there was no denying the silent tears that spilled from the corners of his eyes and ran in rivulets of regret down his temples.

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

Dean was twenty-nine when he realized he needed to be in control…..and when someone taught him letting go was even better.

 


	6. Chapter 6

**Summary for the Chapter:**

> Dean was twenty-nine when he realized he needed to be in control…..and when someone taught him letting go was even better.

**Notes for the Chapter:**

> Please note, this is unbeta’d. Any and all grammatical errors are mine. (And I’m sure there are PLENTY. :))

Dean was twenty-nine when he realized he needed to be in control…..and when someone taught him letting go was even better.

Dean knew all about pain, suffering, screaming in agony when no one would hear him.

Dean knew all about inflicting that same pain on someone else.

Dean also knew the shame of liking that pain and burying it deep inside of him under the proverbial lock and key, never letting it come to the surface of his life.

Because Dean had been in Hell.

And even though he was now out and about and mingling in the world of the living, he had to fight every day to maintain his sanity.  To push his worst nightmares somewhere in the back of his dark mind and keep up the façade of the old Dean Winchester. 

But Dean felt that pain every day. 

And every day he still smiled at his brother and flirted with cute waitresses and basically made an ass of himself whenever he could as he desperately tried to chase that darkness away.

It wasn’t until he and Sammy were on a case that brought them to an S&M club in Nevada called Purgatory that he realized that there may be something better to take the darkness away.

Standing in the closed club at nine in the morning, in his Fed suit, a pad and pen in his hand, he tried so hard to listen to the statement the chick with a leather bustier and a nose ring that had a chain that attached to an earring was giving Sam but his eyes kept straying to the rack behind her.

The rack that eerily reminded him about his time down below.

And it was taking everything in him not to shudder in a mixture of disgust and something else.

Something he would never tell Sammy or _anyone_ for that matter.

Those dark feelings that never wanted to truly go away and seemed to rear their ugly head in the worst moments.

“Dean?  Dean you okay?”

His brothers voiced knocked him  out of his staring contest with what he knew was an inanimate object across the room but it may as well have been breathing and waving at him jauntily for all the life he was giving it with his mind’s eye.

 “Uh, yeah.  Yeah, I’m fine.”  He turned back to Nose Ring and cleared his throat before asking, “So, to summarize, you saw nothing, you heard nothing and you happened to stumble on the body when it was time to close up shop?”

Nose Ring rolled her overly lined eyes and pursed her lips, “No.  What I said was I didn’t hear anything because the music gets pretty loud in here and the private rooms can get a little wild so even if I _did_ hear something, I wouldn’t have suspected that someone was getting their heart torn out of their chest.”

“And what about security footage?”

Dean saw Sam give him a strange look as Nose Ring gave him an exasperated one, “Like I _just said_ , Dude, we don’t have security footage in the hallway for private rooms.  What we got is footage over the doorway for that hallway.  That’s it.”

Exasperated with his inability to stop staring at the various instruments of voluntary torture surrounding him, Dean turned his anger on Nose Ring, “First of all, don’t _dude_ me.  You can address me as Agent or you can address me as Sir, whatever the fuck you prefer.  Second, can the attitude.  A man died here last week and from what I understand no one can tell us a Goddamn thing as to who may or may not have killed him, so if I want to ask the same damn questions fourteen fucking times, I will.”

Immediately, Nose Ring’s eyes cast down and she pointedly looked at Dean’s chest as she answered him with a meek, “Yes, Sir.  I’m sorry, Sir.”

Dean’s breath caught in his throat for the longest thirty seconds of his life as he saw all the will drain out the girl in front of him. 

And damn him if his cock didn’t twitch in his pants at the sight.

Sam cleared his throat a little uncomfortably, giving Dean a look, “Uh, it’s fine, Natalie.  Please ignore my partner.  He, uh, didn’t have his coffee yet and it makes him a little cranky.  Who can we speak to about getting the security footage you _do_ have?”

A door creaked open from behind them and a melodic voice rang out, “You can speak to me.  I’m the owner.”

Dean and Sam turned around to face the woman walking towards him.  Dean heard Sam take a deep gulp and he wondered if his dumbfounded expression mirrored his own. 

Long wavy auburn hair cascaded down her back and framed a pair of intense bright blue eyes.  But what caught Dean’s attention was the way her body was encased in a one piece leather catsuit.  Laces lined the sides at her hipbones revealing smooth creamy skin in between the criss cross pattern.  Matching laces criss crossed over her chest and framed high full breasts.

Sam’s mouth opened then closed as he stared and then blinked before he tried to look everywhere but at the woman in front of him.  Meanwhile, as Dean’s eyes finished their trek from the point of her black patent leather stiletto heels to the top of those breasts, he raised them up to meet her gaze head on.

“Miss Shayla!”  Natalie squeaked, “I didn’t want to interrupt.  But these men-.”

Shayla flicked her gaze over to Natalie and he watched them soften, “It’s fine, Natalie.  Why don’t you see if Mr. Smith in room one needs more water before he leaves, hmm?”

Natalie nodded as she looked down to the floor, “Yes, Ma’am.”  She answered as she scuttled past them and through the door her boss had just come through.     

“So, gentleman, from what I heard, you are looking for security footage?  May I ask your names?”

Sam cleared his throat and scratched behind his ear before bringing out his Fed badge as Dean did the same, “Uh, yes, I’m Agent Young and this is my partner, Agent Bonham.”

Shayla glanced at their badges and nodded, “My apologies for not being here earlier gentleman.  I had an early appointment and was unaware that you would be coming in today to investigate.”  She gestured a hand towards her outfit, “Hence, the clothing.”

Dean licked the inside of his lip, “When you say appointment, you mean you had some poor sucker tied up in there actively asking for you to beat him and paying for it?”

Shayla smiled at Dean cajolingly, “When I say appointment, I mean, I have a client who asks for discretion and unless he is a part of this investigation, I suggest we move on to what you need.”

Oh, if she only knew what he needed right now.

Sam smiled, making sure to flash her a dimple, as he once again gave Dean a look of recrimination, “Of course Ma’am.  So, about that camera footage…”

The whole time Shayla and Sam pulled up the needed footage at the front desk of the club, Dean remained quiet and tried his best not to stare a hole into the lovely Shayla’s head.  Between actively trying not to stare at the contraptions around the room and the exposed skin of Shayla’s body, Dean was giving himself a migraine with all of this ‘not looking’ he was doing.

“Thank you, Ma’am.”  Sam was saying as he pocketed the memory stick he had downloaded the footage of that night on, “If we need anything, we’ll be sure to give you a call.”

Shayla nodded her head at Sam and as they both made their way to the exit, her voice rang out, “Agent Bonham?  May I have a word with you please?”

Sam stopped in his tracks as Dean raised an eyebrow at her in question, “Yeah?”

“Alone?”

Millions of thoughts ran through his head and he tried to figure out what she could possibly want with him.  He didn’t think his silence would equate as charm so it’s not like she was enamored by that.

Sam held back a small smile as he grasped his brother by the shoulder and gave it a pat, “I’ll, uh, be at the car.” 

Once Sam was out the door, Dean turned back to Shayla with a questioning gaze, “Soooo, what can I do for you?”

Shayla’s hips swayed as she glided towards him, her manner changing in the steps she took towards him, aggression suddenly leaking off of her curvy frame, “It’s not what you can do for me, Agent.  It’s what _I_ can do for _you_.”

 Some of his cockiness returned and he lifted his lips in a half smirk, “Oh yeah?  And what’s that?”

She stopped directly in front of him, so close he could smell the musky perfume she wore, “I saw you looking at the toys we have here.  And it was with more than a passing interest, Agent.”

Dean’s smile dropped, “I don’t know what you’re talking about.”

She raised one delicate eyebrow as her fingers toyed with the end of one of the laces at her chest, “Oh yes, you do.”  She turned and sashayed towards the rack in the corner that had been taunting him earlier. 

For the first time, he saw the back of her outfit and he took in the roundness of her firm, high ass encased in the leather she was wearing.  On anyone else, on any other day, he would have appreciated the show but when she ran her hands over the metal bars framing the rack, that thick feeling hit him in the gut again and he swallowed.  Hard.

“Is there something you want, Agent?”  She said in a low tone, before she reached down and ran her hands up and down the metal bars suggestively, her blue eyes burning into his, “Perhaps something you _need_?”

Dean took a deep breath, and forced his face into a scowl, “I don’t submit.  If that’s what you’re asking.”

Shayla gave him a dark smile and turned, leaning against the metal bars, “You sure about that?”

“Positive.”

With a contemplative smile, Shayla crossed her arms in front of her, “Well, I heard you make poor Natalie almost cream in her panties earlier.  _That_ was very interesting.”

“I’m sorry, what?”

“That twenty-something little darling that was here talking to you gentleman before?  She’s a submissive.  And she _loves_ when a man gets all growly on her.  And when I heard you through the door, I thought for sure you were a natural Dom but then I come out here and you can’t keep your pretty little green eyes off of all of our toys and I wondered if it was all a cover up.”  She tilted her head in contemplation, her auburn hair sliding across the leather of her suit with a whisper, “Or are you that unaware of what you want?”

Dean lifted his lips in a sneer, “Listen lady, let’s get a couple of things clear.  One, I don’t pay for tail.  Two, if I want something, I go get it.   And three, I. Don’t. Submit.”

He could swear he saw Shayla shiver from her position against the bars as she hummed low in contemplation before glided back towards him, “I’ll tell you what.”  She returned to standing right in front of him, her body millimeters away from his, “Why don’t you come back here tonight as my special guest and _I_ will submit to _you_.  No payment necessary.”

Dean gave her a suspicious look, “I didn’t think you could do that.  I thought you would be either one or the other.”

Shayla winked at him, “Show’s how much you know.”  Her breath quickened slightly as her eyes slid down to his lips, “I’m what is called a switch.  I can happily do either or.  I just make my living off of being a Mistress.”  She ran her tongue across her teeth, “You should also know that this isn’t always about sex.  It’s about release.  And I don’t mean just a physical release either. I myself don’t always have sex with my clients.  I’m very particular with who I do and do not allow to go there.”  She raised an eyebrow, misinterpreting his hesitation, “As a reminder, Agent Bonham, it is perfectly legal and regulated here, so you should feel safe in that respect.”

Dean looked down at her, staring into her eyes and noticing her pert little nose, so out of place with the aggressive nature of her body language and he couldn’t say he wasn’t a little curious.

Having her body splayed out for him, ready to take it as rough as he could give it….

He bit the inside of his lip as he held back the groan threatening to make its way out.

 Oh, yeah.  He could do this.

“What time?”

*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~~*

Dean was back at the club at 11:00 PM.  He had showered and changed out his black Fed suit and slipped on his blue back up one without the tie and the top two buttons of his white dress shirt open.  After he and Sam had reviewed the security footage, it seemed all walks of life entered the club, but business men seemed to pay for the more pricier option of having a private room and since there was no way Dean was going to wear fishnets or leather, this seemed like the better option.

Explaining to Sam that he was going back to “investigate” the club during peak hours without him, proved to be more difficult than he thought.  Sam didn’t want Dean going to potentially hostile territory without back up and was being hot headed about it.  Finally, Dean had no choice to be semi-honest about his intentions.

“All right, fine,” Dean said with an annoyed huff as he looped his belt through his dress pants, “Shayla invited me back as a guest.  And if I’m gonna rock her world, I’d rather rock her world without knowing my little brother was waiting outside the door for me to finish.”

Sam’s eyebrows raised and he let out a low laugh, “Really, Dean?  Aren’t you a little afraid she’s gonna try and use a whip on that lily white ass?”

Dean pursed his lips and adjusted his suit jacket, “Aint nobody whipping anybody, Sam.”

“Suuuuure.  We’ll see how true that is when you’re walking funny tomorrow, Dean.”

And now, waiting in the main area of the club to be escorted to the room Shayla would be meeting him in, he wondered for the slightest of seconds just how far he was willing to take this.  Watching all of the many scenes being played out around him, noting some of the more intense ones which were not for him, and some of the tamer options that had his heart beating a little faster and caused a bead of sweat to start to form on his temple, left him contemplating what Hell had really done to him.  He knew every day since waking up that he was no longer the same.  He tried to be.  He truly did.  But something was broken inside him.

And he didn’t think the strongest glue in the world was going to be able to put him back together.

“Sir?”

Dean was jerked out of his thoughts by the timid voice next to him and was surprised to see Natalie standing there, pointedly looking at his neck and not his face.

“Natalie.  Hi.  Uh, listen about earlier….”

She gave a small smile but didn’t acknowledge where he was trying to go with this statement, “If you’ll please follow me.  Miss Shayla is in room seven.”

Dean quirked his mouth but let the avoidance slide and followed Natalie down to the hall of private rooms.  A large security guard with an ear piece and wearing a suit stood outside the doorway and nodded his head at him before opening the door for the both of them.  Another security guard stood on the inside of the door with a duplicate suit and ear piece.  This time Natalie spoke to him quietly, “Mr. Bonham is Miss Shayla’s special guest tonight.  She is asking not to be disturbed unless it is an emergency.  They will be in room seven.”

Dean noted with interest as the guard made a notation on a clipboard hanging off of a small table before following Natalie down the plush carpet to a mahogany doorway with the number seven etched into it.  She motioned to the door and started to turn away when Dean stopped her.

“Uh, Natalie?  Hold on for a second.  Has that guard always been on the other side of the door?”

Natalie shook her head, “No.  Miss Shayla posted him here and started having them keep better track of the rooms after the incident.  Before, it was pretty much free reign here on club nights unless you wanted a private with one of the employees.  You and your guest found an available room and that was it.”

Dean nodded, “Thanks, Natalie.”  He said before turning to the door and opening it.

Dean wasn’t sure what he expected, but it certainly wasn’t Shayla sitting in a black trench coat in an armless red velvet chair with her legs and arms crossed, a small smile on her red painted lips.  Around the room were a large bed and various sex toys all new, packaged and ready to open.  Some of them Dean knew what they were, others made his forehead scrunch in confusion.  But in the center of the room was a tame version of the rack outside that made his heart beat faster and his mouth go dry as a desert.   This rack was made to be lay on with a leather bench in between black metal bars with hooks and rings ready for various instruments.

Shayla stood up and started to glide over to him, “Hello, Dean.  Or would you rather, Sir for tonight?”

Dean let out a low hum at her words and couldn’t help but lick his dry bottom lip, “I, uh, I’m not…Listen, I’ve never done this before so I’m not sure what the rules are, if any.”

Shayla reached him and ran a hand over the lapel of his jacket, her bright blue eyes looking up into his with intensity, “Oh there are rules.  Plenty of them.  But we’ll keep it simple tonight and use a color code.  Red meaning stop, yellow meaning I need a break and green meaning fuck yeah, keep going.”  At Dean’s nod she continued, “I like it rough and am pretty much up for anything.  Any hole you want is yours ‘cause I like it all.”  At Dean’s indrawn breath she smirked, “However, I do ask if you take my ass that you be gentle at first.  I didn’t take out the whips and canes because you are not a trained Dom and you may unintentionally hurt me and once I’m in a headspace I may not be able to say no immediately.  However, there are handcuffs, collars, nipple clamps, vibrators, dildos-”

Dean’s eyes closed briefly and took in a deep breath before letting it out slowly and interrupting her, his nerves getting the best of him, “Uh, okay.  I get it.”

Shayla smiled again, and this time there was an almost gentle quality to it, “You may not know this, but I can tell, you need this.  And it’s okay to need it.”  She pressed her body against his, her lips an inch from his own as her breath caressed against the dryness of his mouth, “Now, stop hesitating and take control.”  She dropped her eyes and her arms fell by her side, “Sir.”

Dean groaned at the term and closed his eyes for the briefest of moments wondering to himself if he’d lost his damn mind coming here.  But something inside of him had drawn him in and if he didn’t let it out soon, he was going to explode.

Suddenly, his back went rigid and he felt his eyes harden slightly as he started to circle around her before stopping back in front of her.  His hands moved to the trench coat and he slowly undid the belt to reveal the black lace bra, thong and garters holding up the black silky stockings that were poured into a pair of black stiletto heels.  He hummed in pleasure before slipping the trench coat off her shoulders and threw it into a corner of the room.

“This….is fucking delicious.”  He groaned out before reaching up and sliding his hand into the back of her neck, into her hair, pulling on the strands until her face was tilted up to his, “Look at me.”

Shayla’s blue eyes tilted up to his as he licked his lower lip, “I want you to look at me when I talk to you, unless I say different, are we clear?”

Shayla nodded.

“Uh uh.  Speak.”  He growled out.

“Yes, sir.”

“Good girl.”  He watched as she visibly shuddered at the term and he had to swallow deep before continuing, “You wanna be my good girl, Shayla?”

“Yes, please, Sir.”  She mewled out.

Dean leaned down and ran his tongue over her pulse point before biting down gently and then a little harder as he heard her moan.  He lifted his head and pulled her hip against his growing erection before meeting her eyes with his own, “Good girls don’t come until I tell them to.  Understand?”

“Yes, Sir.”

He shifted his hips against her, growling at the friction, “But you can beg all you want cause I do love to hear my good girls beg.”

Shayla couldn’t stop the whine from leaving her mouth as she brushed her bra covered nipples over his suit jacket, making them rise into hard nubs.

Noticing what she was doing, Dean reached down and slapped one of her ass cheeks, relishing in her moan as he soothed against the sting he created and tsked at her, “No, baby, you don’t get to do that.  I only get to touch those until I tell you different.  In fact, you don’t get to touch your pussy either.  Now, go sit on the edge of the bed.”  

He watched as she followed his order and he let out a small moan at the sight of his handprint on her ass before biting his lip and reaching down, palming himself through his dress pants.  He was already throbbing with need and they had just started.

It scared him how much he needed this.  How the inner turmoil from all he had endured left him feeling broken and while this wasn’t going to heal him he could already feel it soothing a part of the rage that never seemed to fade. 

Shayla expected nothing from him.  Wanted nothing from him.  She was his to temporarily control.  And it made him ache in a whole new delicious way.

Her eyes met his from her perch on the bed and she waited patiently for further instruction, but she had kept her legs wide open and he could see that her thong was pulled between her bald pussy lips and she rocked forward slightly letting the lace rub against her throbbing core.

His eyes narrowed as he made his way over to her.   He reached down and pulled the thong up even tighter against her pussy and relished in her gasp as he moved it rhythmically against her, “Already being a bad girl I see.  Trying to get around my rules?”

Shayla bit her bottom lip and squirmed against the pressure of the thong against her clit, “I’m sorry, Sir.  I can’t help it.  Feels so good.”

Dean hummed before reaching down with his other hand, grasping the thin straps of her thong and ripping them off of her one side at a time, leaving the scraps to flutter to the bed as she gasped, “Such a bad girl.”  His fingers smoothed down the front of her pussy and he let out a sound of pleasure when he found her already soaked, “So fucking wet already.”  He rubbed against her clit with his thumb and playfully flicked it, “Only I get to touch.  I won’t tell you again.”

Shayla’s hips lifted into Dean’s caresses and she nodded, “Yes, Sir.  I’m sorry, Sir.  It won’t happen again.”  She gasped out.

Dean took her hand and brought it to the zipper of his pants, “Take out my cock baby girl.”

Shayla eagerly unzipped his pants and reached into his boxer briefs before bringing out his throbbing cock without unbuttoning his pants.  Her eyes widened at the sight and Dean felt a bead of precome slide out the tip.  She rolled her eyes up to his, “May I please suck it, Sir?”

With a smirk, Dean grasped his cock in his hands and rolled the tip over lips, spreading the moisture before nodding, “Open.”

Her mouth opened eagerly and she rolled her tongue over the tip before swallowing his cock down her throat in one stroke making his eyes roll into the back of his head, “Fuck!”

She hummed over her mouthful and quickly started an up and down motion, letting out mewls of pleasure before she released him and used her tongue to flick over the sensitive head.  Dean quickly released his belt buckle and button.  She helped him pull his pants and boxer briefs down his thighs before rolling her eyes up to meet his as she lifted his cock and ran her tongue all the way down to the base and nuzzled at his balls before bringing one into her mouth and gently sucking it.

Dean’s fingers tightened their grip on her hair and groaned, “Such a good girl.  Knows just what her Sir likes already.”  His fingers tightened even further, “Stop.”  He said firmly, his deep voice reverberating through the room.

Immediately, Shayla stopped, releasing him with a pop, “Yes, Sir.”

Dean shrugged off his suit jacket and threw it to the side before unbuttoning his dress shirt and sliding it down his arms.  He toed off his shoes before sliding down his pants and underwear and removed his socks.  He watched Shayla’s eyes devour every inch of skin that was revealed and her body language was telling him she wanted to touch him but wouldn’t until he said so.

And God help him but it was such a fucking head rush.

Naked, he took her hand in his and brought it to the top of his chest, “Does my good girl wanna touch?”

Her blue eyes shimmered at him as she licked her lips, “Yes, Sir.  So badly.  Can I use my tongue?”

Dean took a deep breath in, “I don’t know if you deserve that yet.  Lean back on the bed and let me see how badly you really want it.”

Shayla shimmied back and leaned on her elbows, her legs wide open, revealing her wet core as it shined in the dim light of the room.

Dean gripped his cock in his hand and stroked it once, twice at the sight before squeezing at the base, “I don’t know.  It doesn’t look like you really want this.”

Shayla squirmed on the bed, rolling her hips wantonly, “Please, Sir.  Touch me and see how much I want you.”

 Dean hummed and ran his hand up one smooth thigh, his finger hooking in the straps of the garter belt, “I think I need to taste just to make sure.” 

Kneeling on the floor, Dean threw her leg over his shoulder and bit at the inside of one of her thighs and heard her gasp into the air as her hips rocked up at the sensation.  He soothed the bite with a swipe of his tongue before sliding his tongue to her dripping pussy.  He gave her one long swipe from the bottom to the top and heard her moan as he flicked her clit with his tongue.  He brought his mouth back down to her hole and stabbed at it, humming as more slick slid out of her, “That’s much better.  Such a good girl getting yourself so wet for me.”  He heard Shayla whine and he felt her fingers against his nose as she starting rubbing at her clit.

Dean’s eyes narrowed and he stopped her hand as he clicked his tongue at her, “Naughty.  I told you no touching.  You’re gonna have to be punished for that.” 

Shayla bit her bottom lip and let out a sound, “I’m sorry, Sir.  I can’t help it.  Feels so good.”

Ignoring her, he grabbed up both of her legs and bent them at the knee, bringing them to her chest, “Hold your legs.  Don’t bring them down until I tell you or you’ll just make this worse.”  At her nod, one eyebrow rose at her as his lips pursed slightly, “Don’t you dare fucking come unless I tell you to.”

Shayla let out a rough breath, “Yes, S-.”

Dean roughly dived in her pussy and sucked the whole thing into his mouth.  Hard.  At Shayla’s cry, he took two fingers and shoved them in before massaging at the rough spot he found in there and brought his lips to her clit, alternating between rapidly flicking at it and laying his  tongue roughly against it.

“Oh, God.  Sir!  Please!”

Dean hummed against her, before lifting his mouth and using his thumb to press down on her clit, watching as she threw her head back against the bed, her fingers grasping her legs so tightly she was leaving behind marks.

“Do you think you deserve to come?”  He asked as he rubbed even harder, “I told you not to touch yourself and you didn’t listen.”

“I’m sorry, Sir.”

Dean slapped at the side of her ass with his free hand and watched as she jerked up and moaned in desperation.  His cock gave a jerk at the sight and he had to fight to keep his own desperate groan from escaping.  “You want it so badly don’t you?”

“Yes!  Yes, please!”

He rubbed at her clit even faster, his fingers stroked even quicker, “You would love it if I stuck my cock in there right now and fucked you into this bed until you came screaming?”

“Yessssss.”

Abruptly, Dean took his hand off of her, “No.”  At her sob, Dean smirked, “Told you not to touch.” 

He reached down onto the floor where his discarded pants lay and pulled out a condom from his back pocket, quickly sliding it over his erection.  He nudged her legs down and reached underneath her as she lay gasping.  Her eyes glittered up at him and he flicked open her bra, releasing her mouthwatering breasts to the room.  He hummed at the sight, before leaning down and sucking one rosy nipple into his mouth.  His cock nudged at her opening and he rolled his hips, sliding it through all the slick. 

He moaned around her nipple and flicked it with his tongue, before sitting up slightly, “Turn over.”

Immediately, she flipped herself onto her hands and knees with her back arched, “Please, Sir.  Please fuck me.  Want it so bad.”

At her words, Dean slid a hand over the globe of an ass cheek, up her back and into her hair before he grasped it in his hand and tugged it back roughly.  He pulled her up to lay her back against his chest, his mouth at her ear, “So eager.  I fucking love to hear you beg.  It makes me so fucking hard.”  He bit at the lobe of her ear, “Are you ready?”

She tried to nod but Dean’s grip on her hair made it impossible and she let out a desperate whine, “Yes.  Yes, please.”

He pulled her head back even further, the column of her neck tight, “Yes, please who?”

“Sir.  Yes, please, Sir.”

With that, Dean pushed her forward and entered her balls deep in one smooth stroke, reveling in her scream as he immediately started to pound in and out of her roughly.  He could feel her start to tighten around him almost instantly and punctuated his words with rough thrusts, “Don’t.  You. Dare.”

Shayla let out a loud sob and he saw her bite down onto the beds comforter as she desperately held back on her orgasm, “Please!”  She begged, “Please, Sir, let me come.”

Dean’s eyes were starting to lose focus as her warm slick walls kept grabbing on to him in earnest.  The squelching sounds of her arousal and his rough grunts started to reach a crescendo and he could feel his balls tightening up indicating he didn’t have long left before he filled up the condom with his come.

He slapped her ass with a loud smack and reveled in her scream as he rubbed away the sting, “Such a bad girl making me want to come so quickly.”  At his words, she tightened herself around him and he let out a strangled noise and he knew he was a goner.  He reached underneath her and started to roughly rub at her clit, “Come.  Now.”

At his words, Shayla let out a hoarse yell and her walls started to spasm around him.  With a grunt, Dean fucked her through her orgasm before he gripped her waist and pounded into her so hard he saw stars as he finally released into the condom with a loud, “FUCK!”

Gasping, he rolled away from Shayla’s heaving back and lay on the bed next to her as she remained on all fours.  He watched as her glazed eyes cleared, her gaze flicking to his as she smirked at him.

“Well, well, Agent.  Looks like you really know how to fuck a bad girl into submission.”  Her gaze hardened, “Now, get your ass on the rack.”

Dean’s eyebrows scrunched together, as his heart started to pound, “Pardon?”

Shayla rolled garter clad hips as she crawled to him and threw a leg over his waist, straddling him.  She reached for both of Dean’s hands and with surprising strength she yanked his arms over his head and pinned them down with her weight, “Did you think that was it, Dean?  Did you think you were gonna walk outta here without getting your own punishment?  Silly, silly man.”

Dean felt his stomach clench in desire and maybe a little trepidation as he looked up into her burning blue eyes, “Wha-what are you talking about?”

A smirk lifted one side of her mouth and she licked at her bottom lip, “You fooled yourself into thinking that the release you needed was me being obedient to you and while you are _very_ good at ordering me around, I think you’ll be even better at taking orders.  Now,” Shayla leaned down and licked at Dean’s neck before biting down roughly, _“Get on the rack.”_  

Dean shuddered at her tone of voice, her words bringing back feelings that he thought he had buried down into that twisted part of him that he never wanted to let out.  That part of him that clawed at his psyche every day and left a part of him a pitiful mess.      

Dean didn’t submit.  Not anymore.  He told himself that he would never be at anyone’s mercy ever again.  No matter how much he may actually want it.

As Shayla stared down at him, some of the hardness in her expression faded and she took a deep breath, “I promise to take good care of you, Dean.  You _need_ this.  You _want_ this.  Let me help you find that release.”

Dean swallowed hard and blinked rapidly before he closed his eyes and let out a long deep breath, when he opened them he felt something in him give in and he nodded, “Yes…..?”

Shayla’s face shifted back to that intense stare, “Mistress will do fine, Agent.” Shayla shifted off of him and stood on the floor in her stilettos.  “Now get up.”

“Yes, Mistress.”

Dean felt like his head was empty and everything around him was fading until all he knew, all he heard was his Mistress’ commands.  He lay down on the bench and obediently allowed her to cuff his hands and legs to the metal bars. 

She showed him where there were safety latches and at any point he could release himself, “But I doubt you’re gonna want that, right Agent?”  Without waiting for him to answer, she asked him, “What are your colors, Dean?”

He stared up at her, the blue of her eyes the only color he could sense in the room.  But he knew that’s not the answer she was looking for, “Red for stop.  Yellow, slow down.  Green, keep going.”

“Very good.”  She said as stepped out of his field of vision.

He could hear water running and he guessed there must have been a sink somewhere in the room.  She reappeared next to him with a wet washcloth and she quickly disposed of the used condom on his half hard member before cleaning his cock and balls with precision, “I like my toys fresh.”  She tossed the washcloth to the side and straddled his waist, “I already washed up at the sink, but I don’t think I cleaned it up enough.  I think my toy needs to stick his tongue way up inside of me and make sure I got every drop of my come out.  What do you think, Agent?  Will you clean me up like a good boy?”

Dean felt his cock give a jerk at her words before he nodded eagerly, “Yes, Mistress.  I want to clean you all up.”

Shayla pinched a nipple in between her fingers roughly, letting out a hum as Dean gasped, “Good boy.”  She pinched his other nipple and let out a low laugh at his yelp, “Oh, yes.  My toy likes it when I pinch his nipples.  Maybe I should bite them next.”  Without waiting for him to answer, Shayla leaned down and bit down hard on a nipple before gently laving it with her tongue, making him cry out, “I love that sound.  Let me see how many times I can make you do it.”

Dean lost count after twenty-five times.  He knew for sure twenty-five times he yelled out in ecstasy at the delicious burn of pain that was on the precipice of pleasure.  After that, the rest was a blur of moans, slaps, and thrusting hips as he licked her out and ate at her with a hunger to appease her that he didn’t know he had in him. He had begged her to suck his cock faster, his hips lifting into her mouth before she grasped him tightly at the base of his dick, effectively stopping him from coming, over and over again. 

He was going crazy.

She was gonna kill him.

He hated it.  He loved it. 

And when she finally slid him inside of her and rode him so roughly his cock felt like it was going to break, she blessedly gave him permission to come.

And when he came, something inside of him finally, finally released.  It was more than pleasure. It was more than pain.  It was something he didn’t know he needed. 

He let go.

After, when he finally made his way back to a rapidly speaking Sam at the motel spouting off lore and his suspicions about it being Skinwalkers that were causing the deaths, Dean only nodded and smiled at his brother affectionately.

“Sure, Sammy.  We’ll go over the lore and see if we can find out where they’re holed up.”

Sam stopped his blathering for one second and looked, really _looked_ at his brother for the first time since he walked in.  His eyes skimmed over his features before staring into Dean’s eyes in contemplation, “You….you okay, Dean?  You look….I dunno…almost….peaceful, I guess?”

Dean let out a small smile and placed his suit jacket over the back of a chair, “I’m good, Sammy.”  At Sam’s earnest look, he let his smile drop and gave him serious eyes, “I’m….better.”

Sam’s eyes flicked over his face one more time before he released a long sigh, “That..that’s good.  I’m glad.”

“So am I.”

*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*        

Dean was thirty-one when he fell in love.  And it scared him shitless.


	7. Chapter 7 - Part 1

**Summary for the Chapter:**

> Dean was thirty-one when he fell in love. And it scared him shitless.

**Notes for the Chapter:**

> A/N: Sooooo, the Dean x Reader part kinda got away from me and I realized that I was over 8,000 words in, rambling my way to the conclusion. So, I decided to break it up. Good news is, the second part is almost finished. :) Thank you so much for all the comments & kudos I’ve had a blast writing this and I’m glad there are those out there enjoying it. I’ve strayed away from exact canon time periods as I’m not following it as closely as some awesome writers do, however, for purposes in this chapter, this portion is set sometime in Season 7. Lisa is in Dean’s past and Sam has his soul back with no memories of his experience in Hell.

Dean was thirty-one when he fell in love.  And it scared him shitless.

Over the years, he’d had more sexual partners than he could count, his job never affording him the opportunity to stay in one place for any extended period of time.  He never led any of them on, always left them satisfied, always making sure they both were on the same page as far as the non-status of their relationship would be. 

Dean didn’t want to be labeled as a fuck ‘em and leave ‘em type but apparently those rules of the road his father had spewed out to him so long ago held some substance. 

Too much tragedy followed him everywhere he went, and he found he’d rather leave ‘em than have any of the women in his life physically hurt in any way shape or form.

Cassie had been the closest he had come to the word ‘love’, and while he had been hurt so badly by her rejection, he realized when revisiting her years later, it had been too easy for him to walk away from her when she finally knew who he really was for him to believe it had been anything more than maybe a puppy love in its most pure form.   

Lisa was his most recent and the last mistake he would make in believing that he could have ‘normal.’  That whole relationship had quickly gone to shit and while he had cared for her and Ben deeply, love was never a word that he uttered out loud because he had never truly felt that he could love a woman the way they deserved.  Especially, when he spent his days and nights in constant fear that something could happen to her and Ben, coupled with being restless living an ‘apple pie life’.  It didn’t help that he had eventually realized that she had been a poor substitute for the aching hole the temporary loss of his brother had left behind.

So, Dean had resigned himself and made himself believe that one night stands were the way to go. 

Unless of course there was a woman that came along that could, surprisingly, kick his ass.

And when that happened, well, the world seemed to tilt on its axis a little bit.

Dean never thought of himself as a true masochist.  A dominant?  Yes.  A submissive?  At times. But one day when a long leg shot out and kicked him in the stomach before bending down into a sweep that dropped him onto his back with a groan….

Well…he was reminded why. 

The reason people and, yes, sometimes even he, embraced pain and put it hand in hand with pleasure.

He’d gladly take another kick to his solar plexus if it meant he could look up at her and see her for the first time over and over again.

Long straight dark hair and light brown eyes looked down at him as one of the most beautiful women he had ever seen stood above him with a gun pointing at his face.

And his gut twisted in more than just pain from that well-placed kick.

“You move, you die.  Now, who the fuck are you?” She said between clenched teeth.  

Dean lifted up his hands in surrender, “Dean.  Dean Winchester.  And you might be?”

Instead of answering, she cocked the gun, “None of your damn business.  Get up.  Slowly.”

Dean complied, his eyes unable to stop drinking in her form.  Black leather jacket over a black tank top and skin tight black jeans tucked into calf high combat boots, rolling over toned curves, her hands and eyes steady as she followed his movements with the precision of a well-practiced fighter.

She was gorgeous.

She was also still pointing the gun at his chest.

“The Winchesters have an anti-possession tattoo.  Show it to me.”

He considered trying to be funny, but the way she held her gun let him know she knew how to use it, so instead he raised an eyebrow, pulled down his t-shirt from his collar and waited as her eyes roamed over the pentagram.

It was only then that she put up the gun and slipped it back into its holster at the small of her back, “Well, Winchester, looks like your reputation precedes you.  Unfortunately, you swaggered your ass into what was supposed to be a trap for the werewolf in town.  So, if you don’t mind, if you could just mosey your way back to wherever you came from, that’d be awesome.”

Dean pursed his lips at her blatant dismissal, “Apology accepted.”  He said sarcastically.

“What the hell do I have to apologize for?  Kickin’ your ass?  Ain’t nobody told you to come here.”

He stepped forward, his eyebrows scrunched together in annoyance, “I’m here for the same reason you are, lady.  To kill a werewolf that’s eating people’s hearts.”

“Well, I _got_ this.  So, _you_ can go.”

And that’s how Sam found them, engaged in a screaming match over who had the biggest balls.

They had known each other for exactly fifteen minutes and already Dean hated her.

Well, he actually kind of liked her too.

When she got really angry, her eyes lightened dangerously, her voice got lower instead of higher and she poked him in the chest with her finger.

Dean wanted to break that finger so bad.  He also wanted to put it in his mouth and suck at the tip until she melted underneath him.

Needless to say, the first six months of their friendship had been frustrating at best and downright tumultuous at worst.  

Mostly because Dean couldn’t figure out if he wanted to smother her in her sleep or kiss her until she made that low moan in her throat that came out when she tasted something delicious. 

He also had a hell of a time trying to just figure _her_ out.  The layers of who she was hidden deep underneath a gruff exterior and smart mouth leaving him dumbstruck when she gave a soft smile and kind eyes to a grieving family or when she turned into a protective mama bear and practically growled when a child was involved in any of their cases.   

It didn’t help that her and Sam got along like two peas in an annoying pod from the moment they met.   It had taken Sam six seconds of puppy dog eyes to get her name that day.

Y/N.

Beautiful, breathtaking, annoying Y/N.

And now?

Whenever the three of them joined up on a case, Sam and Y/N spent hours researching the shit out of them and wallowed in long silences where neither of them needed to speak to one another but they still seemed to know what the other was looking for. 

Meanwhile, whenever Dean and Y/N were in the same room it was as if a fire was lit under their asses and instead of putting it out they spent their time trying to find as many leaves and dried kindling they could to keep it at its hottest temperature.  

Their constant arguments could be as serious as who was going to save the world tonight or as ridiculous as what was better than sex. 

Pie or Y/N’s weakness: Chocolate.

The correct answer was neither. 

But they were both so stubborn they refused to come to an agreement on the subject.

And while he would fight anyone who tried to convince him that his pie obsession was uncalled for, he still managed to pick up her favorite candy bars at various rest stops, making sure to always keep a secret stash in his duffel bag if only to torture her with them as he waved the chocolaty goodness at her from the farthest corner of whatever room they happened to be in.

And when she shrugged as if she could care less before distracting him with a well thrown book, pillow or elbow and tackled him on the ground, wrenching the chocolate triumphantly out of his hands, Dean tried not to think too hard on the way his body buzzed the minute her curves made contact with him.

Or the way he stared at her as she gave him a middle finger and bit into her prize.

She was so ridiculously annoying.

And then, there was the……moments.

Moments of something palatable that rolled its way over the two of them and made Dean feel like there was almost something tethering them together, tightening with each deep breath, each sigh of frustration and each smile that he managed to get out of her.

In fact, if Dean really wanted to be honest, there was one moment that stood out more than the rest.

The three of them had been searching for a Wendigo in a forest outside of North Dakota and they had set up camp around the perimeter of where multiple attacks happened, hoping to draw it out instead of traipsing through unknown forest and getting their asses lost.

It had been unseasonably cold that night.  Sam was up keeping watch wandering around the base of their camp jumping up and down to keep warm.  Meanwhile, Dean and Y/N were in separate sleeping bags laying by a fire that hadn’t been enough to keep Y/N from shivering in her sleep.  Dean had stayed in his sleeping bag for twenty minutes contemplating how hard she would hit him in the nuts if he decided to lie down next to her and try to help her stop shivering.  The decision was made for him when she rolled onto her side and her teeth started audibly clattering and he couldn’t take it anymore. 

Grabbing up his blanket and sleeping bag, he laid his sleeping bag next to hers and wrapped her body under the plaid wool of his blanket.  He lay on his side against her back and after hovering his arm over her this way and that he finally said fuck it and wrapped his arm around her waist, bringing her body flush against his.

She woke up immediately and tensed and he swore he could feel her reach for her gun that she had kept next to her.  But before he could say anything, he heard her take a deep breath through her nose as if sniffing the air, then she visibly relaxed into him, saying nothing.

It was ten minutes later, as his nose was in her hair and he was trying to not make it obvious that he was trying to figure out the scent of her shampoo, (Oranges?  Mangos?), when she finally spoke up.

“What are you doing, Winchester?”

Dean tensed against her and tried to surreptitiously move his face out of her hair, “Trying to make sure you don’t freeze to death, what else?”

She hesitated before answering him and to his surprise moved her body even closer to his, moving until her ass was right up against his now very interested cock and burrowed even deeper under the blanket he had thrown over them.  Dean let out a silent curse as he felt himself swell even more when her delectable backside rubbed against him and he tried his best to picture and name the ugliest monsters he had seen to date in an effort to get his dick to stop being an asshole.

He had finally gotten himself to relax some when he heard her clear her throat, “Thank you.”  She whispered, “This…this is a lot better.”

Dean closed his eyes against the warmth that amplified in his lower belly and took a deep breath, “Yeah, well, the Wendigo aint gonna want no frozen meat, so, gotta keep his dinner warm somehow.”

Y/N let out a harrumph but didn’t move from her position against him, “Moron.”

A half smile graced his features as he felt his body settle into something he hadn’t felt in so long, if ever.  Despite their current circumstances, despite the fact that they were on a hunt and _could_ very well be dinner, he felt….safe.  Warm.  Content.

And before he could talk himself out of the feeling, he felt his heavy eyes finally drift closed and he fell asleep.

The next morning, found him still alive. 

And hard. 

Sometime during the night, he had rolled onto his back and Y/N had rolled into his chest with her arm wrapped tightly around him and her face buried in his neck. Her leg was bent and thrown over his waist, and either Y/N was deliberately trying to get him off or she was having a very good fucking dream because her hips were undulating against him slightly causing her calf to move against his very interested, throbbing cock.

Dean blinked a few times and desperately tried to hold back a groan but he was unsuccessful.  Y/N’s head sleepily popped up and she looked up into his eyes.  He watched as unnamable emotions flickered through the light brown depths as she stared at him, her hair adorably sticking up haphazardly, and he would have bet money she was going to kiss him.  Except his asshole dick chose that moment to twitch in interest and her eyes clouded before she reared back, sat up and hit him in the chest.

“Really, Dean!  We’re being hunted by a monster and yet you still can’t control yourself?”

He hid his disappointment by bringing his arms behind his head as he grinned up at her, seemingly unrepentant, “It wasn’t _me_ rubbing all up on _you_ , Sweetheart.  If you’re gonna offer it, he’s gonna take it.”

Y/N gave him a disgusted look even as she blushed, “What the fuck ever, Dean.  Aint nobody offering nothin’.”

He winked at her, “Sure, Darlin’.  Keep telling yourself that.”

“UGH!” 

And with that, Y/N threw the covers back and quickly made her way to Sam where he was standing at the edge of camp giving them extreme side eye.

While Dean was sure they had killed the Wendigo, the who, what and when’s of it was a blur. 

Because the only thing he could focus on from that moment in time was that split second when her eyes were clear and the guards were down and he saw….something in their depths. 

Something that made him both exhilarated and fucking terrified.

From that trip on, the fire that burned was slowly turning into an inferno and the tension was at an all-time high.

But they still had each other’s back.  Still steadfastly protected one another in dangerous situations, taking hits when it meant they could distract would be bad guys from hitting the others; from hurting the team they had built on a precarious platform constructed from frustration, sarcasm, smirks….and that something else.

He would be damned if admitted how much he missed her when she was gone, on her own, hunting the bad guys on her terms. 

But he did.

And it made him even angrier when he felt _it_.  That something missing, gnawing at his belly and deep inside his chest.

He wouldn’t even touch the emotion he felt when he saw her name pop up on his or Sammy’s phone or the rush of elation when he saw her truck pull up beside them on whatever no name highway they agreed to meet on.

However, it was during a particularly stressful case, where they couldn’t agree if it was a God or a Djinn causing havoc that apparently Sam had finally had enough. 

Enough of them and their unnecessary arguments.

Enough of the yearning dance they had perfected as they circled around one another.

“I’m soooo glad Dicky Dean is coming out to play today.”  Y/N growled as she threw a pillow at his head, the movement of her arm making her breasts jiggle slightly in her tight red tank top.

Not that he noticed.

Dean ducked just in time before casually sitting back in the motel chair and taking a drink of his beer as if he didn’t have a care in the world, “Why am I a dick?  ‘Cause I don’t agree with you?”

“It’s not that you don’t agree with me.  It’s the _way_ you don’t agree with me.  All high and mighty with that cocky grin.” 

Said grin slid across his lips and he shrugged, “I’ve been told I have a _big_ reason to be cocky.”

“Yeah, well, people lie to spare our feelings all the time, Dean.”

“Facts don’t lie, Sweetheart.”

“For the four millionth time, don’t call me Sweetheart, you ass.”

 “Sorry, Baby.  I’ll try not to.”

“Dick.”

Sam stood up, “All right! Enough!  You two are driving me to drink.  As a matter of fact, that’s what I’m gonna go do.  Go to a bar and get a drink and maybe it’ll muffle the sound of this nonsense and we can go back to _actually solving this case_.”

“Wait, Sam,” Y/N said as she stood up next to him and grabbed a jacket, “I’m gonna go with you.  I need a drink too.”

Sam threw his hands up in the air and walked to the door, “Whatever.  Let’s just go.”

Dean blew a kiss at Y/N as she gave him one more glare before sticking her tongue out him and the door closed behind them.

Childish?  Yes.

But that tongue?  He could imagine it doing any number of things to his body and the thought made him groan deep in his chest.

Pretty soon the silence of the room started to grate on his nerves and when he noticed himself pacing over the same space over and over he finally gave in, grabbed his jacket and headed to the bar down the block from the motel.

The music was loud but not too loud and it was fairly crowded for a weekday.  There was any number of available conquests waiting for the kill but his eyes automatically gravitated to the one person who made his blood boil for so many different reasons.

She had discarded her jacket somewhere and was swaying to the current song, standing in front of the digital juke box, vodka club in hand, as she perused the other music selections.   Her round ass encased in her skinny jeans had the attention of most of the bar and if she continued to shimmy it for much longer, she’d have a line of eager suitors ready to roll.  

Dean’s feet started making their way over to her before he had to physically stop himself. 

_What was he doing?  Let her annoy someone else for the night._

He made his way over to where Sam was keeping an eye on Y/N from the bar, beer in hand.

“Was wondering how long it would take you to make your way over here.”  Sam said in greeting.

“I got bored.”

Sam smirked at him, “Uh huh.  And I’m sure it had nothing to do with Y/N.”

Dean gave him a look of disbelief, his eyes following Sam’s stare to where Y/N was laughing with some random male stranger over who knew what, “Why would it have anything to do with that pain in the ass?”

“You guys fight like cat and dog.  And the tension keeps building and building…”

Dean raised a hand at the bartender and deliberately turned his back on Y/N’s form across the room, “There’s no sexual tension, Sammy.  She just makes me want to choke her out.  And _not_ in the good way.”

A sly smile slid across Sam’s face as he leaned against the bar on one elbow, “Who said anything about _sexual_ tension, Sigmund?”

“Shut up.”

Holding his hands up in surrender, Sam shrugged, “Okay.  Okay, Dean.  So, then, uh, I want to ask you something.”  Sam shoved his free hand in his pocket, a sheepish expression sliding over his face, “Ummm, if you’re really not interested, then, uh, you wouldn’t mind me going for it, right?”

Dean stilled as he stared at his brother’s face in shock, “You’re not serious….are you?”

Sam shrugged, “She’s hot.  And she’s smart and brave and can tell your ass off as fast as she can sew you up after getting hurt.”  Sam’s eyes flicked over to her, watching as she picked up a cue stick and started playing pool with the random guys she had been speaking to earlier, “And she has the nicest ass I’ve seen in a long time.”

“Sam!”

“Oh, please.  Don’t start.  I’ve seen you checking it out plenty of times.”

“Yeah!  Cause I have eyes!” 

The bartender finally made his way over to them, “What can I get ya?”

Thanking the bartender silently for the interruption so that he could gather his thoughts, Dean replied, “Whiskey.  Neat.  Thanks.”

The bartender nodded and made his way back to the other end of the bar as Dean took a deep breath and raised his gaze to Sam’s, “Look, things like this can get complicated, Sammy.  She’s independent as hell and prefers to work alone.  Making a relationship like that work would be hard.”

Sam scrunched his eyebrows in confusion, “Who said anything about a relationship?”

Dean shot Sam a confused look his own, “Huh?”

“We’re both adults, Dean.  Sex doesn’t have to equate to a relationship.”

An anger that Dean wasn’t sure he understood shot through his body and he felt his jaw involuntarily clench as he turned his body toward his brothers’, “You sayin’ you just wanna bang her and act like nothing happened after?”

Sam’s eyes scrunched further, “Dean…I’m not sure what part you’re not understanding.  If there’s anyone who _could_ comprehend something like this, it’s you.”

Dean threw his hands up in frustration, “Yeah, Sam!  With random chicks that know the deal and are okay with having a one night stand that’s not gonna amount to nothin’.”

Sam bit down on the inside of his mouth, his lips quirking slightly before he turned it into a frown, “And if I tell Y/N what the deal is and she’s okay with it, what’s the problem?”

With a growl, Dean tossed back the whiskey that had appeared in front of him and wiped the side of his mouth before pointing at Sam, “The problem is that she’s not just some random chick, Sam.  It’s Y/N!  She’s our friend and she deserves more than just some random fuck and a ‘See you around sometime.’.”

“So you _do_ care about her?”

“Of course I fucking care about her. It’s…she’s….SHE DESERVES MORE DAMMIT!”

Sam finally let that quirk at the side of his mouth slide into a full-fledged grin as he drank the last of the beer in hand, “Then why don’t you stop being a dick and tell her how you feel already.”

Dean blinked at Sam, momentarily thrown at his change in demeanor and his mouth opened and closed like a fish as he realized just how telling his words were, “Wha-?”

Slamming the empty bottle on the bar, Sam rolled his eyes, “Get out of your perpetual hole of denial and go get the girl you’ve been in love with for months already.”

Dean stubbornly ignored Sam’s last statement, “Soooo, you don’t want to bang her?”

Letting out a scoff of disbelief, Sam rubbed at his eyes in frustration, “God, please give me strength.  No, Dean. I don’t want to bang her.  I would never, ever get in the way of what I’ve seen between you two.”  He grabbed at Dean’s shoulder and tightened his grip forcing his brother’s eyes to his, “It’s okay to love someone, Dean.  It’s okay to love _her_.”

Dean stilled and stared at his brother as he bit the inside of his lip, a million thoughts racing in his mind.  The most prominent one being the nonononononononono that was echoing in his brain bouncing around like a pinball against the memories of all he had endured.  Every moment in his too short/too long life that had changed who he was before to who he was now.

He didn’t love her. 

He _couldn’t_ love her.

He still had so much darkness in him.  Guilt.  Pain. And he struggled every day to put those feelings of inadequacy into a small corner of his mind until they reared their ugly head at night when it was too quiet to drown out the memories.   

Everything in his world ended in tragedy and tears and so many had been hurt or died because of him. 

He couldn’t risk it.

His eyes flicked over to where he saw Y/N raising her hands in victory before holding her hand out to the poor schlep in front of her.  She playfully curtsied in thank you as the money was slapped into her palm with a grumble.  As she smiled, she turned her gaze towards the bar and met Dean’s eyes with her own and waved the money at him with a smirk and a wink, before letting the smirk drop into a frown as the intensity of his stare seemed to burn her from across the room.

He couldn’t risk _her_.     

Dean swallowed thickly as she gave him a concerned face.  Y/N brushed off the guy currently trying his best to earn his money back and pushed her way through the crowd to them.

He could feel Sam watching him from his perch “Moment of truth, Dean.  She’s making her way over here and since she’s seen you go pale as a ghost, she’s gonna wanna know why.”

Flicking his eyes everywhere but at her, he felt his heart start to pound even faster and panic quickly set in.  He reached into his pocket and flung some money on the bar before making his way to the door.

“Shit!  Dean!  Dean, wait!”

Ignoring Sam’s calls, he opened the door to the bar and disappeared into the night.

He _wouldn’t_ risk her.

~*~*~*~*~*~*~*~*~*~*~*~*~*~~*~*~*~*~*~*~*~*~*~*~  

“Oh my, God!  It’s a Wednesday.  Why is it so fucking crowded in here?”  Y/N muttered as she finally made her way to the bar where she saw Sam standing by himself, his mouth set in contemplation.

Grabbing his arm none too gently, Y/N pulled his attention to her, “Hey!  Where’d Dean go?”

Sam let out a soft sigh and shrugged, “Not sure.”

Ignoring the disappointment in her chest, she pulled up the empty stool next to him and sat down, “What do you mean?  He was just here and he looked like he was gonna puke.  Is he okay?”

Sam let out another sigh and motioned to the bartender, “I, uh, may have said something that he wasn’t ready to hear yet.”  He lowered his head to the bartender when he appeared, “Another beer and a vodka club, please.”

Y/N stared at Sam’s profile and took note of the hard clench of his jaw, “Sam, he looked physically ill.  What could you have possibly said to make him react that way?”

The ridiculously tall hunter’s eyes flicked over to hers before looking away.  He rubbed his hand over his face and then he suddenly shrugged and threw his hands up, “You know what?  I’ll tell you because I honestly can’t take much more of this.” 

“Sam?”

He placed his hands on Y/N’s shoulders and lowered his head to look into her eyes, “My brother is head over heels, madly, _insanely_ , in love with you,” Sam squeezed her shoulders tight, “And at this point I’m convinced, he will never tell you.”

Y/N blinked up at Sam as her mouth dropped open.  She let out small sounds of disbelief before she swallowed hard, shook her head and let out a loud laugh, brushing his hands off of her, “Get the fuck outta here!  No, he isn’t.  Sam, you’re outta your mind.”  She plucked the vodka soda out of the bewildered bartenders hand before he could place it on the bar and quickly swallowed two large gulps before turning her attention back to him, her hands trembling slightly, “Did he…did he tell you that?”

Sam gave her an indulgent, gentle smile, “He didn’t have to.  There’s no one in this world I know better than my brother.  So that means I also know he’s drowning in a denial pool and with each day that passes, he keeps going deeper and deeper and he’s gonna drive both you and I crazy until he either drowns or runs away.” 

“Soooo, he didn’t tell you this himself?”

Sam groaned and slapped himself on the forehead, “Do you two ever listen to anything other than what you want to hear?”

“This _isn’t_ what I want to hear, Sam!  Do you know how stubborn, how controlling, how much of a pain in the ass that man is?!”  Y/N let out a growl, “H-he is constantly trying to tell me what to do.  He’s always challenging every thought I have,” She threw back the rest of her drink; “He’s always nagging me about every move I make.  Make sure to check your six, Y/N.  Make sure you don’t hesitate, Y/N.  Make sure you watch Sammy’s back, Y/N.  Why didn’t you say you were cold, Y/N? Like, what the fuck?!  When we’re in the same room it’s hard to breath _as is_ and he just makes it so that I feel like I’m _suffocating_ when he…when he…”

Sam let out a small laugh as he watched her struggle, “When he what?”

Y/N wiped at the side of mouth, catching a stray droplet of liquor before whispering, “When he teases me and then nudges me trying to get me to smile at him.  When he waves coffee under my nose trying to get me to wake up in the mornings.  When he steals the bacon on my plate because he already finished his and then he fucking _winks_ at me and….and…”  Y/N closed her eyes and swallowed deep, “When he looks at me….with those _eyes_ of his…..” 

Oh, God.

In the months that she had known him, Y/N had pushed whatever she might be feeling deep into the caverns of her heart because she knew, she fucking _knew,_ Dean was never going to address the proverbial elephant in the room.  She would watch him, watch _her_ out of the corner of her eye and would see…she would _feel_ this utter sense of loss coming from him. 

At first, it confused her.  But then the nights she was forced to share a room with them, she would hear him struggling in his sleep, whimpering as memories of pain assaulted his senses and she understood.

Dean Winchester couldn’t afford to feel anything. 

Because everything that mattered was eventually taken away from him.

And Y/N understood.

So, she left it alone.  And she _ached_.  But she left it alone.

She was a proud, stubborn woman and she wasn’t going to force herself on anyone. 

No matter how much she loved him.

_Fuck!_

_Now what?_

A whimper left her mouth and she banged her head on the bar top in front of her and groaned, “Why did you have to tell me that, Sam?  I was just fine doggy paddling in my own damn pool.” 

His large hand rested on the top of her head as he affectionately ran his hands through the strands of her hair, “No you weren’t.”

*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*


	8. Chapter 7 - Part 2

**Summary for the Chapter:**

> Dean was thirty-one when he fell in love. And it scared him shitless. - Continued

**Notes for the Chapter:**

> A/N: Okay Guys! This is it. The second part of Chapter 7 and possibly the end of this fic. I have a list of firsts that can be utilized for future Dean x Reader parts, but I’m on the fence. I can possibly just use them for some side stories but I’m kind of in love with this little world being built here. 
> 
> Let me know what you think!

If Dean kept pacing like this, he was going to wear a hole in the already thread bare carpet of his and Sam’s motel room.

But he couldn’t seem to sit still.  He couldn’t get his body to relax.  And he sure as shit couldn’t drown out his brothers words to him.

He didn’t love Y/N.

He _didn’t_ dammit.

He _couldn’t_.

Because like everything else in his life he was going to fuck it up.  He would somehow end up getting her hurt or breaking her heart or God forbid, get her killed and then he would really be in a world of trouble because living after _that_ was gonna be a touch and go situation.

He liked her.  (She annoyed the shit outta him.)

He respected her. (She knew how to throw a mean right hook.  He may or may not have been on the receiving end of one of them.) 

He trusted her. (Her and Sammy. At his back.  Always.) 

And he damn sure was attracted to her.  (Did she have to wear fucking booty shorts to bed?!)

But love?

Dean took a deep breath and really thought about what he actually felt when he thought about her; was around her. 

And there was no denying he had never felt anything like how he felt for her.  The foreign emotion that bubbled up inside of him so wrapped up in all of his other feelings that it confused him.  And anything that made him feel vulnerable was pushed to the side.  Hidden under layers of sarcasm, whiskey and flannel.   

He shook his head and ran his hand through his hair for the four thousandth six hundred and twenty fifth time tonight. 

There was a jiggle of a doorknob next door and he heard a jangle of keys and a muffled curse as they fell to the floor and his heart leapt in his chest.

Y/N was back. 

And currently being unsuccessful in getting into her room if the sounds and curses were any indication.

A distinct sound of a palm hitting a door echoed down the hallway, “Goddamn it!”

His feet took him to his door before he could really think about it and he turned the knob, opened the door and looked into frustrated and then surprised and then _terrified_ eyes.

“Dean!”  She squeaked and promptly dropped the keys in her hand again, “I, uh, I’m having trouble opening my d-door.”

Dean raked his gaze over her, taking note of her slightly trembling hands and rapidly blinking, darting eyes as she picked up the keys yet again and he groaned as he laid his head against the doorframe to his room, “Sammy opened his mouth didn’t he?”

An audible swallow echoed down the hallway, “I-I don’t know what you’re talking about.  I, uh, was just really tired and wanted to get to bed is all.”

Dean gave her side eye from his perch against the doorframe before pursing his lips and straightening out, “Give me your key.  Let me see if I can get it open.”

Y/N held out the key in her hand and her fingertips brushed against the inside of his palm and she may as well have touched his dick with the way he shuddered at the slight graze. 

Ignoring the strangled sound she let out, Dean stood in front of her and rammed the key into the lock before roughly turning it and successfully opening the door.  He handed her back the key, careful not to touch her, “You, uh, sometimes, you gotta be rough with these old things.  They always need a little extra push.  To, you know, open.  Ahem.”

Y/N blinked down at the key in her palm and let her gaze raise to his, “Rough, huh?”

He cleared his throat again, “Yeah.”  He rasped.

That _something_ was there again.  Pulsing between them.  Roaring with a heat that made him almost want to flinch at the energy that kept expanding and releasing with each of their harsh breaths.

_Jesus Christ._

Suddenly, he was surrounded by soft skin and mouthwatering curves as Y/N grabbed his neck and brought his mouth down to hers and pressed her lips roughly against his.  He momentarily stilled in shock and Dean could feel her stop and start to pull away before he let out a groan of release and pulled her against him, running his hands through the silky strands of her hair, grabbing her around the back of her neck with one hand and bringing her flush against him with the other.  

Y/N let out a moan of surrender and he could feel his heart trying to make its way out of his chest as he pivoted her until she was up against the wall next to their doors.  Her hands slipped under his black T-shirt and she ran her fingers over his chest, a fingertip scratching against a nipple making him jerk against her.

“Fuck, Y/N.”  He groaned against her mouth, before sliding his mouth over cheek and down to her neck.  He let himself take a deep inhale of her scent and his eyes closed as he realized he had started to think of that smell as home.

“Dean….” She let out on a sigh.

Breathing heavily, Dean pushed back from her and placed both of his hands on either side of her head, leaning against the wall, encasing her in the small space.  His green eyes met her light ones and for the first time he was granted with what she looked like when she was turned on.  Her mouth was wet from his kisses, her lips swollen from where he had bit on them and her cheeks were flushed with desire.

She was fucking delectable.

And he wanted her so bad it hurt.

He swallowed and placed one of his hands against her cheek, before sliding it the back of her head and holding it so that her gaze met his head on, “Y/N, please tell me you want this as bad as I do.”

She swallowed shakily, let out a deep breath and nodded, “Fuck, yes.”

Dean let out a low desperate moan at her words and brought her mouth back to his, rolling his tongue against hers and moaning louder at the taste.  Not letting her go, he maneuvered her so that he was walking her backward into her room, slamming the old door behind him.  Y/N grabbed at his T-shirt and helped him pull it over his head before laving her tongue along a nipple, making a strangled sound come out of his mouth.

“Shit.”  He whispered as his cock started to leak into his pants and he held her head against his chest. 

Y/N released him with a small pop and started rolling her tongue down his chest, over his stomach until she was kneeling and had reached the top of his jeans.  She bit lightly at the skin in front of her as she unbuckled his belt and unzipped his pants before roughly pulling them down. 

Before he could even think to ask her to slow down, she had her tongue rolling over the exposed tip of his cock that was sticking out of the top of his dark blue boxer briefs and she whined as she sucked down his dripping pre-come while massaging and squeezing his hard length over the material.

“Holy-fuck-Y/N-wait.”

Ignoring him, she ripped down his boxer briefs to his thighs and hummed in appreciation at the sight of his cock out in full display.  Before he could blink, she had his cock over tongue and down her throat as she moaned wantonly over her mouthful.

“Gah!  Holy shit woman!”  Dean yelled out as he quickly (reluctantly) pulled out of her mouth and reached for her under her arms.  Standing her up, he pulled her against his heaving chest, his cheek resting against the top of her head, “You tryin’ to kill me?”

Letting out a huff of laughter, Y/N tilted her head back with a smile and licked her lips, “Been thinking about that for so long.  Couldn’t help myself.”

Dean let out a groan as his cock twitched between them, “You _are_ trying to kill me.”  He looked down into her twinkling eyes and smiled, “God, you’re beautiful.”

Y/N’s smile faded and her eyes looked down briefly before flicking back up, now filled with earnest, “Kiss me.”  She whispered.

His own smile disappeared and he took in every line, every eyelash, every beauty mark on her face before raising a hand behind her head and burying it in the soft strands of her hair.  He tilted her head back even further before slanting his mouth over hers and sliding his lips over her soft ones with a reverence he had never felt before.  Every hitch of her breath and tremble of her hands on his waist made the feeling in his gut intensify into something that made him want to barricade the door to the motel room and never leave.     

When they both finally ended up on the bed, he only in his now pulled up boxer-briefs, she in her bra and panties, his hands never stopped caressing every part of her that they could find as he lay next to her. The silky smooth feel of her skin against him making him moan into her mouth as her tongue tangled with his.

When his fingers rolled over a nipple through her bra and squeezed she let out a gasp and rubbed her panty clad core against his thigh and he could feel how much she wanted this.  He danced his fingers down her stomach and pressed them against the damp spot at the top of her heat, “Mmmmmm,” He hummed into her mouth as she canted her hips up into his touch, “So wet for me.”  He rubbed even harder as she gasped in his mouth, “Can I taste it?” He whispered against her lips.

“Oh, God,” She moaned as she threw her head back, letting him run his tongue over the dip in her throat.

Dean smiled against her chest and licked into the space between her breasts before mouthing over her covered nipples as he continued to rub up and down over her underwear, “Is that a yes?”

“Do-do you _like_ doing that?”

His head shot up at her question and he quirked an eyebrow at her, “I _love_ eating pussy if that’s what you’re asking.”

Y/N’s cheeks turned beet red and she let out a heavy breath, “Fuck, you’re crass.”

He grinned up at her, “You like dirty talk, Y/N/N?”

She pressed her lips together and shrugged looking slightly embarrassed.

Dean bit gently at her hard stomach, relishing the clench and release of the lean muscle, giving her a second to gather her thoughts before soothing the bite with his tongue, “Cause I love talking dirty if it means it’s gonna make this pussy even wetter.”  He growled out as he pinched her clit gently with his fingertips.

Y/N let out a whine as her hips lifted into his touch, “Shit.”

His face was now at the edge of her underwear and he breathed in her scent and groaned against her skin, “Fuck, you smell so good, Sweetheart. Please let me taste you.  Want you in my mouth.”

“So fucking dirty.”  She gasped out before pushing her underwear to the side and letting out a deep moan as Dean’s tongue laved at her now exposed clit, “Is that what you wanted?”  She asked on a shuddering breath, as she lifted her pussy into his tongue, keening as he started to flick it over the engorged bud.

Dean sucked her clit into his mouth before gently pushing her hand away, hooking the edge of her underwear with his thumb and shoving his tongue deep inside of her, moaning at the taste of her slick flooding his senses, “So fucking delicious.  I want to stay here all night, making you come over and over.”

Running her fingers through the short strands of his hair, Y/N pulled on them, forcing his head up, making him growl in need as a pulse of desire at her roughness made him swell even further and he pushed his cock into the mattress.

“So take off my underwear and do it right.”  She challenged with a raised brow even as she blushed at his intense stare, “FYI, finding my g-spot always gains you cookie points.”  She winked.

Letting out a surprised chuckle, he slid her panties down her legs and threw them across the room before settling between her legs, “And what can I cash these cookie points in for when I inevitably find said g-spot?”

“So confident, Mr. Winchester?”

He winked, “Always, Sweetheart.”

She bit her bottom lip as she mulled it over.  Suddenly her eyes softened and she ran a hand over his cheekbone sighing in contentment when he leaned into her touch, “I’ll tell you about the first time I knew.”

Dean’s breath hitched as he blinked up at her, “Knew what?”  He asked quietly.

Her eyebrow quirked up playfully even as she took in a deep shuddering breath, “Guess you’ll have to find that special spot to find out.”

Turns out Dean could find her G-spot.  Rather quickly as well.  And when he relentlessly rubbed against it with his two fingers while mouthing at her clit, making her arch her back as she came with a scream of his name, instead of grinning in victory, Dean worshipped at her mound and brought her down with a gentleness he hadn’t felt in years.

And when he finally, finally slid inside of her, he made love to her mouth as he made love to her body, slowly building her back up again as he stared into her face memorizing what made her mouth fall open in a gasp.  What made her scratch deep marks into his back that made _him_ shudder with need. 

And mostly, what made her eyes lighten with that special something he had seen briefly on a cold morning in the mountains.

Her guards were down and she was letting him in.

And inevitably that’s what made him reach for her leg and drape it over his forearm as he deepened his thrusts, groaning loudly as she braced her other foot into the bed and met his hard thrusts urgently.

The trust in her eyes, the desperation he knew was reflected in his own, made his heart pound so loudly it felt like a roar in his ears.

“Gonna…Oh God-.”  She whined out as her core grabbed him tight and pulsed around him, her eyes wide open and staring into his as she came.

Dean’s hips started to stutter at the tightness of her pussy and he couldn’t hold back any longer as he thrust deep inside of her and moaned her name so loud he knew they could hear him across the street as he shot ropes of come inside the condom.

When he stopped shuddering, his face buried in between her breasts, he finally lifted his head and looked into her eyes as she gently played with the ends of his hair, “I….Y/N…I…”

Y/N smiled at him gently and brought his lips to hers, cutting off his rambling and kissed him senseless.

He nuzzled at her lips and kissed the tip of her nose before he rolled the rest of his body until she was tucked up next to him with her face in his neck. 

And that same feeling that he had only felt with her, returned.  He was….happy.  Content.

And, inevitably, scared out of his mind.

Cause if she didn’t love him back, he didn’t know if he would be able to handle it.

And he didn’t know how to tell her.  How to let his own guard down. 

How to let _her_ in the way she had so selflessly let _him_ in.

They made love three more times that night, pent up desperation egging them on.  Her body on top of his, taking him so fucking well as she undulated her hips.  On her knees, her hands grabbing the headboard as he reached for her hair and pulled it back in his hands, watching her back arch in ecstasy.  Her lips parting on loud gasps as she wrapped her legs around him and met his thrusts with her hips.

It was rough. 

It was gentle.

It was perfect.

It was everything Dean ever wanted.

Dean knew he would inevitably fuck it all up.

It was the fear.

The fear of losing what he had never thought he needed.  Never thought he deserved.  The fear of being vulnerable around someone who could break him so easily.

It was when he woke up the next morning and was wiping down the mirror in the bathroom after his shower, that he saw someone looking back at him that he didn’t recognize. 

He could see the stress lines at the side of his eyes being turned into smile lines.  He could feel the heaviness in his chest lighten with all of the new possibilities the day could bring. 

And he slowly started to panic even more.

When Dean came out of the bathroom, a towel wrapped around his waist to Y/N’s smiling face, he just stared at her with wide eyes until her smile faltered and she sighed.

Instead of questioning him, as he expected her to, she got out of bed and padded naked to him.  She raised her hand to his cheek and caressed it, making him unconsciously close his eyes and lean into her touch with a shuddering breath. She stood on her tippy toes and placed a soft kiss on the corner of his mouth and made her way into the bathroom, closing the door softly behind her.

Leaving Dean to roughly run his hand through his hair and curse under his breath.

He was scared. 

Scratch that, he was fucking terrified.

She got ready to go to breakfast as if it was any other morning.  And somehow, even though Y/N wasn’t the type of woman to let sleeping dogs lie, she let him be silent.  She let him brood. 

And she still smiled at him. 

Although, it broke a piece of him to see that smile was now tinged with sadness.  Acceptance.  

And when Sam knocked on their door to let them know he was ready to go, a triumphant smile stretched across his face, Dean pretended not to see it waver as Sam took in Y/N’s quiet good morning and tremulously returned smile.

Sam and Y/N’s friendship was close enough that despite Sam’s questioning glance to Y/N, the car ride was filled with their affectionate bantering. And as Y/N leaned forward from the back seat and ruffled Sam’s hair at something he said, simultaneously poking him in the side making him wince, Dean’s stomach dipped with emotion as he realized that he wanted a million car rides just like this. 

He wanted her there always.

He wanted her there in the mornings when he woke up. 

He wanted her at his back when the bad guys were closing in.

And most of all, he wanted her eyes to be the last thing he saw when he finally left this world for good.

So, he let the fear go.

Let it melt into another dimension where it couldn’t touch him anymore.

Because she was worth it. 

Dean found himself itching with the need to reach behind him and bring her to the front seat so that he could feel her body pressed against his side, her arm around his waist, his mouth pressed to the top of her forehead.

But now that he had made the whole situation awkward, he battled with himself as to how to make it right. 

Lucky for him, apparently scrambled eggs, bacon and a greasy diner made Dean into a helpless romantic. 

Because as he watched Y/N laugh at something Sam said, a small piece of cheese from her omelet clinging to her bottom lip, he reached over from his chair at her side, wiped away the cheese and held her chin in between his thumb and forefinger and blurted out earnestly, “I love you.  So much.”

Sam coughed and spit out his coffee back into his mug as Y/N blinked wide eyes at him.

“I’m sorry I couldn’t say it before.  When it counted.  I’m sorry that I’ve been a complete ass all these months.  And I’m sorry that I’m a fucking coward who made the best morning of my life into a shit show.”  He grasped her cheeks gently in his hands and pressed his forehead against hers, “ _I love you_.”  He whispered again intensely against her lips, wanting her to swallow the words and have them slide down her throat and into her body for safekeeping.

Y/N’s lower lip trembled against his before she pulled back, searched his eyes and then smiled wide, “You are such a moron, Winchester.”  She reached up and grasped at his hands that were still holding her face and squeezed, “So, do you wanna know when I knew?”

Dean’s forehead scrunched at her abrupt change of subject, trying to ignore the disappointed drop in his belly, before remembering her proposition from the night before, “Knew what?”

She rolled her eyes, “Knew when I loved you more than chocolate.  Duh.”

Dean’s heart skipped and his fingers trembled, “When?” He said lowly.

“The first time I kicked your ass into the ground and your body bounced and you glared at me with those pretty green eyes of yours.”  She said with a cheeky grin.

He fought a smile and mock scowled at her, “You surprised me.  You got lucky.”

She leaned forward, her eyes serious, “I sure did.”  She said against his mouth, capturing his lips with her own for a brief kiss before sliding her mouth over to his ear, “I love you.”  She whispered.

Sam groaned from his chair, “Yuck.  I reeeeally didn’t think this whole matchmaking thing through if I’m gonna be subjected to this for the rest of my life.”

Dean let out a shuddering breath as he brought his lips to her forehead and took a deep breath of her scent, (Definitely mangos.), “I should be so lucky.”


	9. Chapter 8

**Summary for the Chapter:**

> Dean was thirty-one when he fell in love. One month later, he realized he may be ill-equipped to keep it.

**Notes for the Chapter:**

> Soooo, I couldn’t keep my filthy little paws off of this fic and decided to write another chapter. Thanks for all the awesome feedback! You guys are awesome!

Dean was thirty-one when he fell in love.   One month later, he realized he may be ill-equipped to keep it.

It had been bliss. 

For the first month. 

Frankly, Dean was surprised it had taken that long. 

They had been at a bar at a boutique hotel in a large city and his beautiful Y/N was doing that thing she does with her nose when she wanted to get something out of someone.

Namely men.

When she wanted to get something out of _men_.

She was smiling up at the potential suspect, her body encased in a flouncy flowered sun dress with a ridiculously low-cut top as she wrinkled that cute little nose up at something the soon to be dead man said. 

Dean growled low in his throat when he saw the guy place a hand in the small of Y/N’s back as he leaned over to whisper in her ear.

“Yeah, that’s enough of that.” Dean snarled, “He just officially became Captain Hook.”

His chair made a screeching sound as he abruptly sat up and made to move his way over to his girlfriend and chop off the hand of the guy brave enough to touch her when Sam’s hand shot out and grabbed at his forearm.

“No, Dean.  Sit.  Don’t you dare mess this up ‘cause you’re jealous.”  He said with a firm shake of his head, his long hair swaying with the movement.

Dean pursed his lips in indignation at his brother, watching as Y/N gave him a quick frown, “Pfft.  I’m not jealous.  Aint got nothing to be jealous of.  So what if he’s a doctor with blindingly white teeth and a mansion.  Y/N’s not into that.”

Sam rolled his eyes and gestured for his brother to sit, “Yeah, she likes pain in the ass Hunters who don’t know how to let her do her job.”  Sam sat back as he sipped his beer, “You gotta trust her to do her thing.  All signs are pointing to this guy being the lure for the vampire nest.”

Dean sat down with a huff but not before he sent a dark look Y/N’s way, “I trust her.  I don’t trust _him._ Especially since he keeps putting his hands all over my woman.”

 Sam sighed, “Y/N would cut you if she heard you talking about her like that.”

Dean couldn’t stop his grin, “Nah.  She _thinks_ she doesn’t like it.  But she loves when I get all growly on her.”

Sam snorted, “No. She doesn’t.  Now sit back and observe or leave and I’ll be her back up since you can’t seem to control your caveman instincts.”

Dean felt his mouth settle into a pout, “Not being a caveman,” He mumbled, “Just don’t want the guy to touch her is all.”

As he saw Sam roll his eyes again and watch the bar, he really sat back and thought about his reaction to what was going on. 

Dean watched as Y/N sent him warning glances over the guys shoulder before smiling up at the possible suspect and raising a bare shoulder as she flirted shamelessly.

And as his gut twisted again, his breath was caught in his throat as he realized that he _was_ jealous.  All those feelings of inadequacy bubbled up from his stomach into his throat to effectively choke him off.  His eyes took in the custom-tailored suit, expensive shoes, coiffed blonde hair and smooth unscarred face and it made him bit the inside of his lip in the unfamiliar feelings. 

Not the inadequacy part.  That he was more familiar with than he liked to say.  But he had never been jealous before.  Not of another man.  Not of the what if’s that the other man’s presence brought to him. 

Cause while he didn’t always love the Hunter life and the misery it could bring to his existence, he had accepted a long time ago that this was who he was meant to be.  And when he had been lucky enough to find Y/N and the peace she brought to his life, he felt himself doing more than just accepting. 

He felt himself actually _living_ again.  

And now, watching Mr. White Teeth fawning over Y/N and charming her with what Dean was sure was promises of yachts and trips to the Mediterranean, Dean felt not only jealously but regret.

He wanted to give her all of that and more.  But all he had to offer her was an old Chevy, (granted it was the best car in existence.  But still.), and himself.

And he knew he wasn’t enough.

And that made the jealousy quickly turn into stupidity and then anger.

Stupid, unnecessary, un-called for anger.

And he knew that.

But he foolishly allowed it to control his next actions anyway.

Cause as he watched, the suspect took his mouth and brought it to Y/N’s ear and whispered into it before briefly scraping those stupid white teeth over the lobe, then tilted his head so that he could take a deep breath at her neck.

Inhaling a small bit of the essence of Y/N. 

And as Dean felt the red overwhelm his senses, the only thing that kept reverberating through his skull was one thing:

Every bit of _everything_ that was Y/N was Dean’s.

And this dick just made a mistake in thinking he could lay claim to any part of it. 

This time the scraping of Dean’s chair was overshadowed by the bang it made as it tilted backward and hit the floor. 

And Sam wasn’t quick enough to stop Dean from marching up to the bar, seemingly oblivious to Y/N gently pushing the perp away, before grabbing onto the back of White Teeths stupid suit jacket, forcefully pulling him back with one arm until his body stumbled away from Y/N and into the empty bar stool behind him.

“Hey!  What the fuck?”  White Teeth shouted.

“Please.  Have a seat.”  Dean growled, his eyes boring into the asshole, making the man instinctively flinch at the unwavering stare.

“Who the hell are you?!”

“I’m the guy that’s gonna make those veneers into chewing gum.”

“Dean!”  Y/N admonished, “What the _hell_ are you doing?”

White Teeth shot Y/N a surprised glance before bringing his eyes back to the imminent threat, “You know this guy, Katie?”

Y/N’s teeth were clenched as she glared at Dean, “Yes.  He’s my-.”

“Boyfriend.”  Dean growled.

 _“Ex_ -boyfriend.”  Y/N ground out.

Dean felt his heart plummet into his stomach and he quickly broke off the staring contest with White Teeth as he set devastated eyes on Y/N, “Wh-what?”

Y/N took in a deep breath and gritted her teeth, pointedly avoiding Dean’s stare, “I’m sorry, Patrick.  Dean has had a hard time letting go.  Seems he can‘t take the word no for an answer.” 

Dean blinked slowly at her, “Y/N, I think you’re-.”

Y/N’s eyes turned cold, “No, Dean.  That’s the point.  You _didn’t_ think.”  She coolly dismissed him with her gaze and turned her attention to somebody behind Dean, “Sam, do you mind taking your brother outta here?  Somewhere he can cool off and get back into the right frame of mind.”

Sam’s worried eyes were darting between the three people in front of him and he gently pulled on his older brother’s arm.  Dean’s eyes were still set on Y/N’s face, his chest rising and falling rapidly as he blinked at her, hurt bleeding out as she continued to avoid his stare.

“Come on, Dean.” Sam said firmly, “We got other places to be.”

Too stunned to stop his brother from being pulled out of the hotel lobby, Dean’s legs moved numbly towards the door as he heard Y/N apologize to ‘Patrick.’

“I’m so sorry about that.  Now, you were saying about the beautiful property you own outside of town….

Dean didn’t hear his response as the glass doors shut behind him and his brother.

*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*

Sam dragged Dean over to the Impala waiting in an alley around the corner from the hotel, “Dude!  What the hell??!  You could have cost us this case!”

Dean stayed silent as he mechanically entered the driver’s side of the car.

“Dean!  What is your problem?  You’ve never stopped Y/N from working a potential suspect before.  Like ever.”

Dean finally turned his gaze back to his brother, “Yeah, well she wasn’t mine before!”  Dean slammed the door shut forcefully, “And apparently, she’s not mine now.”

Sam shot him a frustrated look from his perch outside of the car as he leaned on the passenger side window, “She didn’t mean it, Dean.  She’s just trying to get the possible location of their nest in hopes that some of those girls are still alive!”

With firm lips, Dean tapped on the steering wheel, “Go back inside and keep an eye on her.  I’m gonna go back to the motel room.  Call me if you need me.”

“But Dean-.”

“NOW SAM.”

With a frustrated sigh, Sam lifted his hands up in exasperation, “Fine.  Whatever.  I’ll call you.”

It was two hours later, and he was sitting at the table in their motel room, four glasses of whiskey in, when Y/N returned from the bar, or wherever the hell she had been. 

Dean had wallowed in his anger tinged despair and had probably picked up his cell phone over a hundred times, his finger hovering over her name, typing and then deleting various forms of texts consisting of accusations, apologies and begging.

Frankly, he was disgusted with himself and his inability to take control of the situation and straighten it out properly.  In his heart of hearts, he knew Y/N didn’t mean it when she called him her ex-boyfriend and he was being a total douchebag about the whole thing, but nothing could erase that feeling of anguish that had hit his senses when she had said it and had so causally dismissed him. 

In their brief time together, Dean had already ingrained her so deeply into his soul that he felt like she had ripped something out of him.

It had hurt.

Dean didn’t do hurt well.  When he hurt, he shut down.  And when he shut down, well, Dicky Dean came out to play.

And he had a hell of a time stopping him.

Dean barely looked up from the laptop in front of him as Y/N slammed the motel door behind her.  Her wedge sandals taking long strides to him as she threw her purse onto the chair nearest the door.

“What the fuck, Dean?!  What was that all about?”

Dean took a casual sip of his whiskey as he lifted one shoulder into a feigned, nonchalant shrug, “Guess it doesn’t matter now does it?”

Y/N ripped her jacket off and threw it at his head, “Are you on crack?  ‘Cause you’re seriously acting like a crazy person!”

He coolly reached up and plucked the denim jacket off his head and placed it on the chair beside him with nary a flinch, “Not acting like anything.”

 Y/N glared at him as she placed her fists on her hips, “I’ve been trying to get the location of their playpen for days and I was so fucking close!  And you just swoop in and try to save a day that didn’t need saving.”

Dean’s upper lip twitched before promptly falling back into his cold unaffected look, “You’re right.  You had it handled.  Don’t worry about me getting involved anymore.  Won’t happen again,” He stood up before he made his way past her and into the kitchenette and poured himself a refill. He raised the glass in Y/N’s direction and pointed at her, “Once this case is over, we’ll just go our separate ways and that’ll be that.”

For the briefest of seconds, Y/N’s eyes clouded over in panic and Dean’s stomach did that twisty thing that only she could get out of him and he felt his guard lower slightly and he could almost feel the misery leaking out of his eyes.

But instead of getting an apologetic Y/N, he got an even angrier one.

Shit.

“You stupid _ASS_!  Did you really think I was breaking up with you?”  She reached up and pulled at her hair letting out a frustrated growl, “God, I didn’t think jealousy would make you this dumb!”

Dean slammed the glass down onto the counter, “This isn’t about jealousy, Y/N…okay maybe it was at first.  That douche couldn’t keep his paws off you but then it became more than that when you treated me like garbage!”

Throwing her hands out to her sides, Y/N gave him a look of exasperation, “What did you expect?  A fucking parade when you turned into a caveman and threw our lead to the side like a sack of potatoes?  There’s _lives_ at stake here, Dean.”

He came around the counter and into her personal space, “Don’t you think I know that?!  I _know_ that, Y/N,” Dean’s hands hovered in the air by her face before running them through his hair instead, “But at that moment I didn’t care! He….he was touching what’s _mine.”_

Her light brown eyes narrowed, and she glared up at him, her finger poking into his chest as her voice lowered to that dangerous level, “I’m not a possession, Dean!  You don’t _own_ me!”

“Yeah, well you own _every_ fucking part of me!”  He yelled into her face as she blinked up at him dubiously, shuddering at his words, before he brought shaking hands to her face and cradled them in between his palms, whispering, “ _Every_ piece of me.  And I happily give it over to you every second.”  He lay his forehead against hers, “God, the thought of losing you…..”

Y/N sighed shakily against his lips, “Dean, it was a fake fight.  I didn’t mean it.  I would _never_ mean that.  _I love you_.  When are you gonna start believing that?”

He swallowed deeply at her words, briefly closing his eyes, “I do.  I do believe that.  It’s just……I’ve had so much bad in my life that the thought of losing the good…..it breaks something in me.  And then it gets me angry as hell that I can’t control myself.”  He raised his forehead from hers, “I’m…I’m sorry.”  He whispered as he looked into her eyes.

Y/N sighed deeply as she looked away from his penetrating stare, “Jesus, Winchester.  I swear I have never been a sucker for a pretty face before, but you……”  Her eyes flicked back to his and she pursed her lips, “Being my boyfriend does not mean you get to control me, Dean.  It only means that you love me and stand by my side.  Not in front of me.  I don’t need protection.  I can take care of myself.”

“I know that.  I do.  I just….”  Dean sighed and bit his bottom lip, “I love you…so much….and sometimes……I don’t feel like I deserve you and….it makes me a little crazy.”

Tilting her head, she leaned forward and pressed her lips to the pulse point at his neck, making him shudder at the touch of her soft lips.  She slid her hands up into his hair and pulled firmly at the strands, holding him to her, “You are everything I need.  Just you.  Nothing more.  Nothing less.” She bit at the skin in front of her, causing him to let out a low moan before sliding her mouth to his ear, “Now, let me show you.”

Dean stood still as Y/N’s fingers slid to the front of his jeans and palmed his semi-hard cock. (It was always at attention in her presence.  It was a wonder they ever got anything done.)  She leaned her head back and stared into his eyes before moving towards his lips, her eyes never closing as her mouth met his, penetrating his gaze, making sure they conveyed what words couldn’t.

“Y/N….”  He whispered against her lips.

Letting out a trembling breath, Y/N opened her mouth under his and ran her tongue slowly against his bottom lip before gently biting down and tugging it with her teeth.  She ran her hands under his gray t-shirt and scraped her fingernails over his nipples before pinching them both between her fingertips,

With a growl, Dean abruptly picked Y/N up under her ass and wrapped her legs around his hips, before bringing her to the closest wall and leaning her up against it.  He swallowed down her cry with his mouth and roughly kissed her, his tongue rolling against hers in earnest.  His mouth left hers and slid its way down to her throat murmuring nonsense against her skin as she roughly ran her hands through his hair and threw her head against the wall.  Her hips undulated against his jeans and he could feel her searching for just the right angle as her breaths started to leave her mouth in deep gasps.

His hands shook as the adrenaline brought on by the thoughts of losing her because of his stupidity suddenly left him and was replaced by a need so deep he let out a sound that sounded suspiciously like a sob. 

He would be embarrassed, angry at himself even, if anything else mattered but her.

Gently, Y/N brought her hands to his face and raised his gaze to hers.  Her eyes searched his for the briefest of seconds, before she leaned forward and brought her lips to his temple, pressing a chaste kiss there before tightly wrapping her limbs around his body.

Dean closed his eyes at the feel of her form against his, his heart pounding wildly in his chest reverberating against the steady thump of hers. 

They stood there for the briefest of minutes before Y/N slowly released her limbs from around his body and slid to the floor.  Gently, she pushed him back with a smile and made her way around him to the bed, her dress fluttering behind her, before she sat down on the edge of the mattress.

Dean’s eyes took in her soft, tanned skin and dark straight hair, watching with bated breath as she slowly lifted the skirt of her dress up her thighs.  Her eyes intensely stared at him as he started breathing heavily across from her, his hands twitching with the effort of not touching her.  The outline of his cock practically pulsed in time with her movements and Y/N hummed and bit her lip at the sight. 

When the dress reached the juncture of her thighs, she stopped moving it up and opened her legs wide.  The gray cotton thong she had on underneath was already soaked through, the wet spot dark against the lighter color.

“Fuck.”  Dean groaned out and reached down and briefly palmed himself, deliberately holding himself back from approaching her on the bed.  Waiting with anticipation to see what she would do next.

With a slow smile, Y/N leisurely ran a hand over a cloth covered breast, squeezing a nipple before sliding it the rest of the way down to the wet spot between her legs.  She brought two fingers to the top of her heat and rubbed slowly watching Dean’s slightly open mouth let out a woosh of air when she pushed the underwear to the side revealing her glistening pussy briefly before covering it again with the wet material.

Something animalistic in him reared up and Dean immediately started to make his way over to her.

“Stop.”  She said in a low commanding voice.  She pointed to a chair directly across from her with her free hand, “Sit.”

Unwilling to refuse her anything, Dean sat down on the plastic motel chair and leaned back in the seat.  He raised an eyebrow at her and made a gesture with his hands as if asking her ‘What now?’

“Now, you stay until I tell you different.  Got it?  Do.  Not.  Move.”

Letting out a low growl at her commanding tone, Dean felt his cock twitch eagerly in response, “Whatever you want, Sweetheart.”

Satisfied with his answer, Y/N leaned back on one elbow as she stared into his intense gaze and slid her fingers into the top of her thong, finding her hardened clit and letting out a low mewl as she rubbed against it.

Dean bit his bottom lip, holding in the groan he wanted to let out and reached down to squeeze his cock through his jeans, “That feel good baby?  You like playing with your clit while I watch?”

At his words, Y/N started to rub harder, “Feels so fucking good.”

“Take off your panties.  Lemme see.”

Y/N gave him a slow sinful smile as a knuckle popped the material up before it slid down to her entrance, “I don’t know, Dean.  You were very naughty today.”  She let out a trembling breath as she buried her middle finger inside of herself, “Perhaps I should just make you watch as I make myself come. Make you go to bed with a hardon.”

Dean couldn’t stop the low moan that slipped past his lips as he watched his girlfriend masturbate in front of him for the first time.  The thought of being punished for his bad behavior making his stomach twist in knots of anticipation, instead of sorrow.

He was such a sick puppy.

And she indulged him in all the ways he needed.

“But then I’d be punishing myself too,” She said as her finger started to move faster, “I’d be depriving myself of that fat cock of yours.  Don’t know if I’d be able to go to sleep without having it in me.”

At her words, Dean’s hand squeezed harder between his legs and rolled his head back at the delicious feeling.

“Maybe seeing it would be enough,” Y/N gasped out, “Take it out for me.”

Not having to be told twice, Dean quickly undid his belt, button and zipper and dragged his jeans and underwear down mid-thigh, letting his throbbing dick out into the air, pre-come already glistening at the top.

Y/N hummed at the sight, “Mmmmm, rub that in for me.  Right there at the tip.  Yes, that’s it.”  She hissed when he complied with a low grunt as his hips canted into the air involuntarily.

Dean’s eyes met hers with a plea as he slowly kept rubbing at his tip, “Please, Baby.  Take them off.  Let me see.  Wanna see that beautiful wet pussy.” 

Y/N bit the inside of one cheek as if contemplating his request, “Well, it is getting a little hard to touch myself with only one finger.  Gonna need more room ‘cause I need at least three to even make me remotely satisfied.”  With that, she stood up in her wedges, her calf muscles standing out in stark relief as she turned away from him.  She reached under her dress and grabbed at the edges of her thong with her two thumbs before deliberately bending over as she slid them down her legs, the back of her dress short enough that he caught a glimpse of her shaven pussy glistening at him.

“Fuck, Baby,” Dean gasped out as he squeezed at the base of his dick, “You’re really trying to kill me here.”

She sent him a smile over her shoulder before quickly removing her sandals and sitting in the middle of the bed against the headboard.  Her dress was hitched up once again, with her knees bent and her legs opened wide, giving him an unobstructed view of her core.  She quickly ran two fingers up and down her slit, before shoving them inside herself roughly, her head automatically falling back against the cheap wood of the headboard at the sensation, “Fuck.  So good.”   

Dean’s hand started to move in time with her thrusts, caressing himself with long strokes from root to tip, twisting at the top.  He started to pick up speed as he watched her fingers curl just so, hitting the spot that always made her scream the loudest.

“Rub your clit for me, Baby,” He grunted out, “Do it the way I do.  The way that makes your thighs shake.”

Letting out a low moan, Y/N complied, bringing her other hand down and rubbing her engorged clit roughly, her breath coming out in loud hitching gasps. 

He could tell she was almost there, red highlighting her cheekbones, a small patch of sweat gleaming from in between the exposed top of her breasts. 

Groaning, he reached down with his other hand and lightly pulled at his balls as he continued to stroke his cock, “You’re so close.  I can almost taste it.  But you know what you need.  Give yourself that third finger, Sweetheart.  Push it deep.”

A loud whine slipped out of her lips as she complied with his instructions.  One, two, three strokes and her eyes started to cross, her thighs began to shake, “Gonna…oh my _God_ ….gonna come! Dean!”  She yelled out as the wet sounds her core intensified and she came with a loud shout of completion.   

Dean’s hand had a mind of its own as his strokes sped up in earnest and all the blood in his body seemed to rush down to his cock, releasing his orgasm with a snap and he came with a curse, his hips canting up into his strokes, ropes of it shooting into the air and running down his hand.

“Fuuuuuuck.”  He said gasping, “That was…..just….”

“So.  Fucking.  Good.”  Y/N said with a grin as she brought her fingers up to her mouth and sucked on the juices still glistening there.

Dean’s cock twitched in interest at the sight.

“Really?”  Y/N said on a breathless laugh, “Even after all that?”

Dean shrugged, an unrepentant grin on his face, “With you?  Always.”

Y/N’s smile softened, “Come here.  Need to feel you.”

Dean quickly undressed and slid his naked body next to hers on the bed as he helped her out of her dress and strapless bra.  His mouth nuzzled at her neck, before laying back bringing her to lay across his chest.

He let out a contented sigh before grinning to himself, “I got a couple of candy bars on the way back to the motel, if you’re in the mood for chocolate.”

Y/N lifted her head and looked at him, “First of all, there is never a time that I’m not in the mood for chocolate.  Second, I thought _you_ thought we were broken up?”

Dean glanced away briefly before looking down at her, “Guess I thought I could bribe you with chocolate if worse came to worse.”

“Smart man.”


End file.
